Selling at PLG Companies

feat. Sam Taylor

Sam Taylor is one of the most experienced Sales leaders in Product-led Growth businesses. In this interview, he shares his experience at Dropbox, Quip, Loom, and Endgame, and discusses how these high-performing PLG companies approached Sales. He discusses the challenges that arise around prioritizing accounts, laying in Enterprise sales, working cross-functionally with Product teams, and using data on product engagement in the sales process.

Transcript

0:21 Derek Steer: Sam, great to have you. Thanks so much for joining me today. It would be great if you could start just by introducing yourself and talking in particular about some of the product-led companies where you've worked.

0:42 Sam Taylor: Happy to do it and thanks for having me, Derek. It’s fun. I’ve been on a journey on the product-led side for a number of years. I'd say I really cut my teeth back in 2011 joining the Dropbox team early on. And so, I stumbled my way into being one of the first five sales members of that team and without knowing it at the time, really went through a pretty transformative period as we were figuring out, I think, the early innings of what product-led growth/product-led sales looks like.

I was there for about three and a half years. I joined a small productivity startup called Quip. It was about 20 employees when I joined. We were acquired by Salesforce in the summer of 2016. And so, I'd actually begun my tech career originally at Salesforce, and so going back to the mothership, so to speak, through a different light.

And then most recently, I was leading the global revenue team at Loom, and so was VP of Revenue overseeing our direct sales, customer success, global support, RevOps, and sales assist motions. It really was my first foray in seeing more of the multi-discipline strategy and how do we think about tying those things together.

And then now, three months in, I've joined a company called Endgame as CRO, and we are building a product that is in service of helping these sales teams use product data more elegantly in their motions. That's what I'm up to today.

2:08 DS: So, you've gone from selling in an environment where product data plays a really big component to helping other companies work in that same way. What has that transition been like? I know it's still early.

2:20 ST: It's early but I'm finding a lot of energy where I don't know how long I'll be able to wear this hat, but in essence almost being a voice of the customer and also being a subject matter expert on how these teams think about deploying not only their strategy, the process, the tooling and then ultimately the workflows that they want that motion to take place.

I feel like I'm able to actually wear more of a product hat than expected in the early innings here, which is really fun and energizing. I think also a broad stroke takeaway thus far is everyone does it slightly differently but the themes continue to be the same in terms of the problem areas, and so really fun to get the validation and pattern matching that we're seeing across our customers.

3:02 DS: Let's talk about those themes for a second because a lot of your roles stand in contrast to working at Salesforce, which is not a product-led company. That is a much more traditional top down.

3:13 ST: Let's throw the bodies at it. Yeah.

3:15 DS: Let's throw the bodies, more traditional, I would think. But I'm curious what are the things that all of the PLG companies have going for them or the way that they operate that is different from a company like Salesforce?

3:29 ST: This is not to say that Salesforce is not a systems-oriented entity, absolutely it is. I think on the product-led side, the interesting shift in power internally is that the product or growth function is going to command a lot more of the strategy and a lot more of the sway, if you will, in the decision making at the company.

What I mean specifically around that is if you're in a sales-led enterprise organization, the lifeblood of that company is going to be the revenue that that sales organization is able to drive, so that voice of the customer, the impact of that sales organization, the retention metrics that you see across all the things, that is the driver.

You can find yourself having a lot more centricity around specific customer feedback in those environments versus in a product-led organization, your acquisition strategy is obviously going to be much more around a self-serve orientation both from folks hopping in and exploring your product for the first time and ideally, early monetization movements.

When I think about the breakdown in revenue ownership of what the product-led versus direct sales component of these companies, Dropbox back in the day we're talking 92:8 or even the early innings, it's less than that. At Loom, it would be closer to 85:15 or 90:10 depending on how far we were in our journey there.

And so, it forces a different level of prioritization and also a difficult level of solutioning, which points towards the product side versus the direct hand-to-hand combat that can be sales.

5:11 DS: In a company where the revenue side and that's sales – I imagine in marketing to some extent – but what traditionally you would think of as the org underneath a CRO if it's only contributing – let's call it 15 percent on the high end – what is the role of those organizations? If you had to write a mission statement for those organizations, what would that sound like?

5:39 ST: I think twofold. One, you're on the hook for insights from a customer base and helping drive the insights around one, where is value being driven beyond the individual user. I think depending on the type of product that you're selling, there can be individual user personas, there could be maybe team workspace, org level dynamics that are taking place.

There's only so much that you can really glean from the engagement data that you're seeing across those user behaviors. There's a broader story and impact to how that is being delivered across an entire company. The discovery process that these teams were running, the business cases that they're having to build, those sorts of insights around how that product is driving value at scale, deeply important.

Obviously, you're on the hook for revenue as well. I think that one of the major areas that becomes the decoupling between these motions is many times the folks that are coming in organically, so to speak, into your product and product-led growth orientation are not going to be the same people that are economic buyers or the key decision makers. It's not necessarily, particularly in a large company, the CEO, the VP, the C-suite, that is a part of that user base that you're going to have in a PLG motion. And so, tying those two things together, I think, marrying the bottoms-up momentum that you're building ideally through your product with the tops-down orientation of what it takes to influence and get a deal done, connecting those two different motions together is the mandate and the mission.

7:20 DS: One of the things that seems really challenging about this is understanding what deals require a salesperson to get done. Because I think one of the things that gets associated with product-led growth in a lot of places is self-serve purchasing motion. In a lot of product-led companies, the entry-level products are in fact self-serve and get purchased by swiping a credit card.

I'm curious how you think about setting rep targets or even the department target? How do you figure out what the right amount of revenue to contribute is? Wrapped up in that is attribution too, I'm curious how you think about assigning credit to the sales team when a deal gets done?

8:04 ST: You led with my first instinct which is, it's about swim lanes and attribution to start. I think when I say swim lanes, are you mapping out the different customer journeys that you would expect and the outcomes you would expect? More specifically, we'll take Loom, for example. During my time, there you can have individuals that are gaining a ton of value on Loom. You have folks that are part of a workspace that are gaining a ton of value.

There can be multiple workspaces within a company. If you're a salesperson, you might look at an account that you're working and there's a shotgun of different teams that are leveraging Loom in different ways. Now, unlikely that all of those different workspaces are going to consolidate on their own. It could happen, but unlikely that that would take place.

Second is unlikely that they would self-select into understanding and realizing the path to either upgrading to an enterprise plan, if you're looking at that as your upsell or upgrade path, or are you looking at a more blanketed or broad deployment beyond the organic usage that's taking place.

An example there is great if I'm looking at setting a target for the sales team, we should be having a decent understanding of what is our baseline in terms of the growth rate that we can expect across these smaller self-serve organizations, what is the incremental lift that we are expecting a sales team to drive. And I'd say, as you get more mature in your motion as a team, you can really start to actually look at the net or delta in terms of what the sales organization is driving versus where folks came in at.

I think the funky part about it is this is not a static entity. And so, in many product-led motions, you're going to have, whether it be usage-based, whether it be license-based, there's going to be growth or potentially contraction that's happening on a daily, weekly, monthly basis.

And so, I think a challenge that a lot of companies have experienced and haven't been immune to in my career as well is how do you set the watermark of what an account is worth from a dollar value perspective and then how do you credit or drive attribution for the incremental value that a sales motion is layering on top of that.

I will say in the early innings, we default towards let's get the learnings and let's have sales engaging and we're not going to have there be stringent rules around that incrementality. Once you're getting beyond your first few sets of reps as you're proving out your sales-led motion or layering in product-led sales on top, that's where you start to get it much more defined in terms of the efficiency there.

10:47 DS: Let's talk about how this might work at companies of different scales because what I find interesting about what you just said is with Loom or Dropbox, the products have value from a single player perspective, right? They might be products that you sell into an enterprise and you sell lots and lots of licenses or you sell a lot of usage, they can be valuable as collaboration tools, but they can also be valuable for an individual.

11:14 ST: Yep.

11:15 DS: I'm curious how that dynamic changes when you're selling to a 500 person company versus a 5,000 person company. Is there a material difference or is it really just the same thing no matter how you slice it?

11:29 ST: The complexity comes into the approval and budgeting processes more than anything. Ideally, you're having consistent value that you're able to drive. I think where the early innings of a business case or ROI journey or analysis that you're trying to use to go and justify budget, broader deployment, etc., is that you want to, in an ideal state, be able to prove that there is a network or compounding effect of more players that are in your product engaging the higher value that you are driving. And the more that you can increase the density of those interactions, the higher value that you're seeing.

We would literally, at Dropbox back in the day, have visualizations of the network map of how different users were connected in terms of their sharing connections. It was anonymized so it wasn't about the individual but it would show over time “Hey, you have a much more connected workplace and let's start to attribute value to those connections.”

It's not necessarily a one-to-one in terms of here's a line between two shared folders and that equals a dollar in value, but you start to see that this is truly a collaborative layer as opposed to an individual folder that's sitting on someone's desktop and being able to use that as leverage when you're talking through these business cases.

I think the other piece of this that becomes more front and center is as you go higher and higher into – we'll call it upper mid-market and enterprise type companies, so we'll say 500, 1,000, 5,000 employee companies – you're going to need to be much more strategically aligned. What I mean by that is doing your diligence where you are engaging with an executive, you have an understanding of their business priorities at the company level, and how are you attaching your product and what your product is delivering to those different initiatives.

And that becomes much more of the focal point and much more around make or break, in addition to obviously the bottom-up motion that's taking place at the user level, but ultimately that's what helps in the prioritization and ultimately getting those deals done and budgeted.

13:35 DS: You just said prioritization, and I think it touches on something about product-led businesses that are unique, which is you started off by saying that all this information about Dropbox, for example, the connection is the sharing between one user and another. That was useful as part of the story that you would tell when you were in the sales process.

But what's special that I see is it's also useful in the prospecting motion as well because you have all of that information before you're even engaged in a sales process.

14:04 ST: Yes. The challenge that most of these companies – I'll eventually almost say any of these companies with a large user base – are experiencing is particularly as you have a sales organization, who should you talk to and why? And why is that a good use of your time? And more importantly, why is that a good use and a value-add that you can go and drive with this potential prospect within an account?

I think that that has been, as we've seen the proliferation of tech, the personalization, the how do you get more specificity around why someone should be engaging with you, for what reason, and how you're going to help, is an ever-going challenge. And I think many of us have experienced in our email inboxes that there can be a lack of personalization that falls pretty flat along the way.

The greater the scale on the user base, the greater the insights and the greater the systems that are going to be required to help pinpoint who you should reach out to and why, what's that compelling story.

15:08 DS: One of the biggest challenges that we had with this back when I was at Yammer more than a decade ago was the question of when you should reach out to someone who has not come through the product first.

Dropbox might be the exception where probably everyone or the vast majority of the market has signed up for a Dropbox at some point even just for their personal stuff. But for many folks, Loom still is new in the market, there are a lot of people who haven't used it. When do you go and do a top-down outbound sales motion instead of looking at your list of the people who came up through the product?

15:49 ST: This is where you really have to be structured in capturing your learnings from early customer conversations. And specifically around, we'll take a Loom or Dropbox or Quip, I basically built a career on horizontal productivity tools that can be used in a myriad of ways. While that's amazing because there's so many different ways that you can drive value for an organization, it can become challenging in terms of the pattern matching, particularly in the early days because you're going to get a bunch of different use cases, a bunch of different organizations that are leveraging your technology. And it warrants how do you focus, because if you say that you're everything to everyone, “Are you anything?” would be a framing in question.

16:31 DS: One thing that stands out about that is these horizontal products all have big markets. I'm curious how much that's required. There are exceptions, of course. Figma is a really good example of a market that’s focused on a very particular user type, the designers primarily and then secondarily developers, but they've made a very big business in a product-led way with a particular target.

But I think a lot of the product-led businesses that I can think of are horizontal in part because the markets are just so massive. I'm curious if you think this problem can even be avoided. Because if having a really big market is a critical piece of being a successful product-led company, then everyone who builds around a product-led motion is going to end up with this same kind of challenge of “Hey, who is our audience, really? What do we market and to whom?”

17:27 ST: Yep, and I don't think it's a challenge that can just suddenly be magic wanded to go away. I have found that there becomes an inflection point particularly as you start bolstering your sales organization and your marketing efforts, where you want to be more defined in guiding people towards example use cases, personas that you want to sell to, how are you going to be more targeted.

Really ultimately, that's a narrowing of what are going to be the set of bets that we make, that these two to three personas are the right starting place or where we're going to go deep and ideally prove out a bunch of success, and then begin layering on as we have more and more data to support that that is a repeatable motion.

In the very early innings, you're going to have a lot of spread across these different personas within a company. I think the area where you start to look is who are our healthiest customers, who are the most engaged, and who are actually getting the most value. What can we glean and understand from the dynamics of those teams, how those deals came to fruition, and then from a bottoms up perspective within the user base, actually how did the user acquisition take place and what does health look like, and then really doubling down on how do we go and do our best to repeatedly drive our most successful customers, is the framework that we used in the past.

18:52 DS: It sounds like this is going back to a little bit of what you said earlier about the role of a go-to market organization at a PLG company partially being to get feedback to tie the story of the customer into not just the sales process in the future but also into the product, and to get that mechanism for the product and future development that ultimately is going to drive more adoption.

19:15 ST: Yep, I agree. It's interesting where in the last – we'll call it five, seven years – the concept of a sales assist team is one that has gained a lot of steam.

To kind of define that at a more specific way, having folks that are engaging with your free or paid user base but the self-serve portion of your funnel where you want to have conversations and gain those insights, you want to help them towards buying decision of some kind. These are typically going to be very short cycle, transactional deals that don't really warrant a full quota carrying seller to be working.

In scaled organizations like a Dropbox, those teams actually serve as the feedback mechanism for what should be productized over time, what experiments are working, what are gaps that we have in the different flows on our self-service journey that we think that we can identify with humans, and then productize and become more efficient throughout the way there.

The goal there is how do we frankly just goal people not on revenue and goal people on satisfaction and customer and MPS – call it what you will. And I think that those teams, particularly as you have larger and larger user bases – so call it a Figma, a Miro, a Dropbox at that kind of scale – that's where it becomes really interesting where you decouple the insights at scale from being a responsibility solely of the revenue team or at least your sales organization, because the volume of data points I've seen becomes an issue.

And what I mean by that is if you're a leader on the product side and you're taking a look and you're working with your growth team and you've got millions of users, your data set is massive. Now, you wheel in your mid-market or enterprise sales organization and they're talking about trends that they're seeing across those conversations, those data points are going to be in the tens, if you're in a really solid spot.

It could even be anecdotal in the very early innings, and so that tension between, it's not statistically significant but it doesn't mean that it's not accurate in terms of the reality of what your sellers are experiencing. Figuring out that translation exercise is actually, I think, a really core role of product-led revenue leaders as well to help broker that feedback loop.

21:39 DS: What kind of advice would you give to a leader in a product-led org that is going to start doing more enterprise sales, because that is a somewhat politically fraught challenge?

21:51 ST: If you're a leader that's stepping into a product org that's going up market and enterprise, I recommend that one, you sit down with your peers on the executive team and you define enterprise. I think enterprise is actually a catch-all term and it means so many different things to so many different people. And the follow-up of not only just the term enterprise but the concept of what enterprise readiness means.

Now, I've seen particularly on the product side of the house, there can be moments where enterprise just means it's not self-serve and so we want to have consolidation plays. There can be an enterprise plan. There can be an enterprise-sized customer you're selling to.

And I think really what you're trying to boil down to is what are the ways that we're going to have a common definition and goal around the types of enterprise customers that we want to go and get. An example of a conversation that I'd recommend folks have is, from an industry perspective or looking at your ideal customer profile in the enterprise, who are we going to support, who are we not going to support. An example being like we're not going to support regulated industries off the bat because their security and authentication and all the things, requirements for them to even say yes to your product are going to be way up here and we're not ready from a roadmap perspective to support that.

Now, on the flip side, you have a typical catch-all of something like “Great, we offer SSO and that's our enterprise plan offering” and that's probably not enough for you to have a differentiated experience and go and drive. And so, finding that middle ground between highly regulated or even maybe requests for an on-premise version of your product that you definitely don't want to support in the early days, but having enough meat on the bone around what are you doing to actually drive additional value as well as additional administrative capabilities to go and capture that demand in that segment.

23:44 DS: It's so funny you say defining enterprise as the first thing because it brings me back to my own experiences particularly a mode where to marketing enterprise meant, Let's go get on the gardener magic quadrant because enterprises care about that when they purchase.” Then within Salesforce, we had a very specific number of employees where if you were above that number of employees, you were now an enterprise account.

You may not have necessarily purchased in an enterprise kind of way. In fact, one of the largest customers, the purchaser, was a manager or had a manager title and there wasn't a big political sale that involved lots of departments the way that you would think of enterprise sales traditionally.

It is kind of funny we found that problem over and over again that people will be talking about enterprise coming from different perspectives and mean totally different things.

24:39 ST: It also does shift the way in which you have to think about leveraging the product momentum, if we want to call it that, as you're using that in your sales cycle. Because the farther up the security requirements chain you go, you're really viewed as a threat, like the shadow IT pushback is significant.

And so, it's also been interesting to see culturally within certain companies that you would deem as enterprise. They're not being as warm a reaction to the groundswell of individual users that are signing up for and taking action. I've seen extreme cases where people are actually threatening to shut down or shut off the usage of that, which you absolutely don't want to do.

There's a different level of tact and mentality that, of course, you have to apply in terms of how you're approaching that account, but I also think that's a hefty education for your team internally as a senior leadership team around “No, it's not just rainbows and butterflies that people are heavily engaging with your product, we have to be sensitive to the lens through which other people are looking at that.”

25:46 DS: I'm curious a little bit about when that did happen to you. Because remembering back to my days at Yammer, I would have thought that that would have been common, that getting in through lines of business, having this groundswell and then taking that and going to sell it to a centralized IT department, as Yammer was doing, I would have thought that that would have upset the IT Department because it feels a little shady, you're going behind their back to some degree.

Most of them were just happy to see the engagement statistics. So, the response very often was “Whoa, we don't have other products that get used that much.” And that solves a big problem because shelf wear is a real issue in big enterprises. People pay for stuff and don't use it. On the other hand, Yammer in particular could be used for anything. You could talk about anything, same way you can in Slack, same way you can in any number of products. And so, we had to prove out the value of Yammer over email in some of these cases where it was “Okay, well, we love that it's engaging but is it valuable?”

26:48 ST: Yep. I think the line – and again, to be clear, if this is exception versus rule, I would say the majority of my experience has been what you just described. “We don't want shelf wear. There's clearly a gap in our offering internally, there's a reason why.” I will say the vast majority of folks are approaching that from a place of curiosity and wanting to support as opposed to shutting down.

I do think, depending on the type of product that you have, internal versus externally facing content becomes a hot topic. Whether that be a shared folder for Dropbox, whether that be a Loom that's recording a screen, etc., that can raise flags quickly, particularly for a security team within IT. And so, being sensitive to that and coming from a place of supporting towards a solution versus – let's say Dropbox, the very early playbook, like very earliest innings, I won't say it was like a ransom play but there were so many people using Dropbox. Many of us were approaching those conversations going like “What are you going to do?” You have to buy this thing because your users have spoken and unless that was done tactfully, that can backfire.

27:58 DS: It’s interesting, I once spoke with the sales leader who defined the sales team's role as bypassing objections and effectively said that we wouldn't necessarily need a sales team if everyone just agreed that they should buy our product on its own. The thing that we do is we get past the objections, and it sounds like part of the product-led world is that there's a very specific type of objection that you need to really get honed in on.

I'm hearing two things, really. One being that it's about focus on a particular user type or building out use cases and stories for the different types of personas to whom you will sell. But also, there is a particular focus on security and other similar objections where your objections are less about “Are people using the product?” and more about “How do we wrangle it as an organization and make it work for us?”

28:53 ST: Yeah, and I would also say another framing on that is you're there to help facilitate a buying process, and the buying process at an individual or team level probably doesn't warrant there being a salesperson involved because they can self-serve that flow.

When you think about larger deployments or broader deployments that aren't going to be as organically driven to a conversation we were having earlier, it's just there's a lot more that you have to go through in terms of building consensus, generating buy-in, influencing folks that may or may not be aware of your product offering and its value but getting them to say yes in terms of both prioritization and ultimately budget. That facilitation is where a ton of the work comes in. And I think there's a number of methodologies that are out there that are around like building champions, helping influence within the organization, but also ensuring that you're getting above a particular power line where someone does have decision making and budget authority and the facilitation of mapping that out and helping drive towards hopefully a positive outcome for the sale that you're trying to do is the goal.

30:04 DS: I want to shift gears a little bit and talk about how systems support this motion. What's different about the technical systems that you would use on a sales team or in marketing or the other revenue generating components, what's different in a product-led org versus a more traditional company like Salesforce?

30:24 ST: Yeah, in a product-led org, you’re reacting to “Where are their hotspots within pockets of usage and accounts that you think is worthwhile to prioritize?” The maturity curve for a product-led organization in the early days – let's use the word outbound – you're outbound in my views like you're being proactive trying to go and generate conversations that lead to pipeline and you go and close that aren't coming through a passive or inbound funnel that you currently have.

If someone's raising their hands saying, “I'd love to talk to Derek,” great inbound. “I recognize that Derek's a person that's interesting that I want to go and reach out to and I'm doing that proactively.” I'm doing a version of outbound. That's very different than a cold outbound motion. You're not receiving a cold email, there’s a compelling reason because you're engaged in the product.

Being able to help highlight, identify, and create a structured way to prioritize, what are the accounts, what are the teams, and ultimately what are the people that you want to be engaging with and sell to, that is where the systems get oriented. In a more traditional direct sales organization, you're either going to have someone filled out – I'm being tongue-in-cheek here – but someone filled out a web form and said, “Give me a call. I want to evaluate your widget factory,” great. Or I call you up and say, “Derek, I think you’d love our widgets, you want to talk?” It's a bit more binary and I think the systems component that I see being the intersection between the product data that exists within your user base, the translation exercise of how does that apply to entities. And in this case, an entity is an account, and then within an account there are teams and individuals and ultimately it does boil down to people talking to people. You don't take action on an account, you talk to people, and then how do you help put people in a position to understand trends that are taking place within the user base to help facilitate those conversations.

That's one piece of it. I think as you continue to move up larger and larger deals, we were talking about moving from a mid-market sale, so we'll call it 200 to 1,000 employee companies is a cut that I see a lot of companies is doing – everyone's got a different definition – or even the enterprise where you're getting 5,000 plus. The difference there is going to be the marrying of who's in your product that you want to engage with or at least what are the trends that are happening across that usage, and then pairing that with “Okay, but who are the folks that actually have the decision making authority and being able to go and tell that compelling story to them?”

33:07 DS: One of the things that you left out is you're not really trying to generate additional product usage in other departments, it sounds like, as part of the sales process anyway. You're not going for “Hey, how can we spur product usage in these adjacencies?” It sounds like it's much more focused on the buying dynamics and the budget holders, the people with authority to make a purchase and just lasering it on them.

33:33 ST: I think that depends on the – another spicy word is definition of virality – do you have true virality within your product and can you hinge or expect that there will be growth that takes place?

I think something that I see frequently in terms of the buying dynamic – or excuse me –in terms of the user-based dynamic is that within a team or a department, you can see growth happening organically. So, you have a set of individuals that started with something, now it's within the marketing organization.

Brokering and making the leap over to a sales team or the product organization or engineering or whomever it may be – depending on the product that may or may not be happening given the use cases, how it's being applied etc., the workflows that are being utilized for that product – that's where I do see there being elements from an education perspective where – let's say that we're selling to the COO of a company and that COO oversees operations, marketing, and sales – you may have organic usage that's taking place within your marketing organization, but you haven't really made it on to the op side.

And so, part of that sales process typically is going to be we'd want there to be some kind of proof of concept. We want to prove it out that it would actually be engaging and compelling for a broader set. Let's bring in folks across these different departments and let's set criteria for what success looks like. Let's time box this. Let's go and do this evaluation.

And through that process, you are actually driving more usage because you're opening up new departments or teams that are being exposed to your product. But that should be a time-based thing, and you're driving towards a specific outcome with those actions. And that's something where, as a go-to market and product organization, you need to be well defined around what sorts of deals or what sorts of opportunities do we want to support in that way, just because the resourcing like in essence, you're almost doing the post-sale launch in a pre-sales capacity in order to get people hooked, seeing the value and wanting to say yes to a broader deployment.

35:49 DS: I'm curious whether you think that sales teams at companies with product-led growth motions should compensate their reps on that specific thing, on the expansion from one department to a completely different department that might be totally cold, no sign ups yet in the product at all.

36:08 ST: Again, it goes back to that definition and expectation on virality and if that jump can be made.

I think that I see a number of different ways that people do it. I've been pro compensating on expansion, especially if we have an understanding of what the beginning stages of health look like, we know there's going to be a time component that it takes to grow into that level of health at scale, and how do we then incentivize reps for a certain time window in terms of the growth that's taking place.

The thing that we're actually trying to counteract by doing that, in my experience, is overselling. So, if you're truly a land-and-expand model, you've got the dynamics, you've got the NRR that supports “Hey, let's just go get a bunch of smaller deals” but those deals are hard one, it's tough because you're probably not going to be able to stack up enough of those transactions in a certain time window, whether it be a month, a quarter, a year for how you're compensating those reps.

And so, when you're going from purely self-serve towards your first innings of having a sales team, I've seen that work well. I think once you hit a maturity curve where you have a very good understanding around what would happen over a multi-year period, if those accounts went untouched or they were not sold to and you can start to get a very strong sense of what the true incrementality is for those reps and that you could get much more defined in terms of what you are or what you're not paying out on, and I think really what that hinges on is like the true definition for your business of what net new revenue looks like and what incremental revenue looks like.

37:48 DS: That's interesting. It sounds like what you're suggesting is you could even pay sales people in advance on some of the future growth knowing that that's just a common thing that happens within your customer base, right? If you really do have a product where sharing is a core component such that you definitely expect more usage the following year but…

38:12 ST: I think there's a world in which if you have that level of conviction and understanding of your customer base, that one, from an efficiency perspective, if you're looking at a one-year time horizon of what the true dollar value closed for that sales rep is and your percent payout that you're delivering to that salesperson in terms of commission, that that being weighted in a more sales rep friendly way. So, the efficiency isn't there because you know you're going to make it up in a 12- to 18-month period.

I don't fully believe in compensating on “Hey, someone signed a terms of service” and we hope because they said in a discovery call that they're going to end up doing 200k worth of value when we pay that rep out on day one on the 200k value. I think there does need to be proof that is taking place. And so, that's where I see these time windows around expansion being something more common that I've seen.

39:07 DS: I want to go back to something you said earlier about the usage of product data or it's kind of marrying what's happening within the product with information about a sales process.

I'm curious where the challenges have been in your career in doing this successfully. And are there companies you've worked at that have done it better than others? What does it look like when it's great? And what does it look like on your way to great?

39:36 ST: Yeah, so I've seen multiple flavors of it. I think the most difficult thing to capture is the concept of momentum.

There are going to be things that are constantly shifting in terms of the way that you have multiple players that are playing in this game called your product and some are more active at certain times than not. There may be times where more people are gravitating towards using solutions, there may be times where they're not. And so, how do you capture the right window of opportunity to leverage that or tell a story around that within your sales cycle?

I think in the early days – and I'll use Quip as an example – so Quip was 20 people and I was pleasantly surprised when I joined that they had a really, really robust intranet that allowed us to see workspaces and the delta week over week or day over day of what was happening across a bunch of different parameters.

Now, not ideal because you had to go and pull this information out. It wasn't being surfaced to you proactively. But from the jump, I was able to see week over week trends and you could get a sense of “Oh wow, we've got acceleration that's happening. I should really prioritize engaging with this team, engaging with this account in a positive way or a negative way,” right? “Oh crap, something just fell off the map. Let's go have a conversation and understand that better.”

Outside of that, I think you'll traditionally see that folks will supplement having a version of a BI tool that maybe you have a data team in lockstep with a RevOps team and you're trying to get account level and potentially power user level views of what's happening. And that is initially decoupled from the other sales systems that you're using. An example being Salesforce, where you've got reps that are working leads, they're looking at their accounts, they're doing the reporting, their logging activities in one interface, and then they're going over here to try and understand how they should be prioritizing the day, their week, whatever it may be.

I do think that those BI tools are getting pretty solid. In a more mature organization, you're going to see that be like a tableau. And so, the question then is workflow, and how do you begin to think about more compelling ways to keep focus for your sales organization. I think there's a lot that's out there in terms of statistics around percentage of salespeople's days that are actually spent selling versus researching or doing non-revenue producing activities.

And I think the goal over time is how do you go and get that sense of momentum and prioritization of actions that should be taken and do that in a compelling way.

42:20 DS: You mentioned Quip’s intranet.

42:24 ST: Yep.

42:26 DS: Now, there are products that are available that do some of this as well without having to do a fully bespoke data pipeline and build it into a BI tool and everything, right? There are products like Endgame, that I would imagine would be pretty useful for this sort of thing.

42:41 ST: A hundred percent. And I think that the area there is going to be around one, how do you have a solid understanding of what should or shouldn't be prioritized? And so, combining both what's happening within the sales motions and the outcomes that you've driven, but also what's happening in real time across the customer information or user information. Tying those two things together is challenging.

And the second piece of it is rep workflow. You want to have things that are absolutely driving a ton of value at the systems level, but there still is action prioritization that needs to take place for the selling capacity that you have on your team and making sure that that is an intuitive and elegant experience is the goal as well.

43:21 DS: When you think about setting up these systems, what's the perfect amount of rep engagement with them, in an ideally configured system, that includes Salesforce and maybe something like Endgame, and you've got Outreach or Salesloft, other tools like that?

How much time do you think reps should spend working in those systems, putting in data or searching for things, doing research as opposed to actually selling?

43:51 ST: I don't have an hour breakdown for you, but what I should say is that at the end of the day, a rep should feel like, “I have maximized the number of customer-facing interactions that felt valuable and strategic and that was much more of my time than data entry or searching for data.”

And I think that you mentioned, what does the sliding scale of not-so-great heading towards great,I don't I still don't think that we've completely nailed as an industry what excellent might look like. I think that story is still to be written and part of the journey that I'm currently on. But I do think that bouncing between disparate systems and leaving reps on the hook for tying those different things together in terms of how to prioritize their day and also what story and action they should go and take, is one that is not efficient, whatsoever.

And so, I do think for rep input into this process, having a RevOps team as they're looking at their stack, ensuring that they've got folks that are on the ground that are going to be a part of these workflows day in, day out, weighing in and ensuring that this is actually creating a more streamlined experience for them as opposed to just adding more complexity and more systems that they have to go in. And so, in the same way that you would have your buyer journey, like your customer in this case, is the folks that you're trying to go and have selling in a highly productive way, making sure you're adding to that productivity story as opposed to detracting.

45:25 DS: I'm curious what you think of as the job of RevOps in this PLG world. Because the data team is involved somehow probably, especially if you have a BI tool that's surfacing the product information or if you're getting information from a data warehouse or product database and bringing it into your sales systems.

What should RevOps be doing? As a sales leader, how do you want RevOps to partner with you in that world?

45:52 ST: I've always viewed RevOps as a strategic partner. And what I mean by that is, as we're thinking about themes for a coming year, quarter, whatever the timeframe may be, and particularly through the lens of how do we drive the outcomes that we want and how do we do it, particularly in the last 18 to 24 months in the absolutely most efficient way possible, getting alignment around the strategy. So, what are the themes that we want to go and drive on, but really the delivery of then how do we have the processes and systems that are in service of that and that flow through.

Now, I think, depending on the organization, how it's structured, there are other things that can get tied into a RevOps organization. An example of that being sales enablement. And is RevOps on the hook for actually doing the enablement work themselves? Is there another delivery mechanism? I think that just depends on organizational structure.

But when I think about a senior RevOps leader partnering with someone like myself in a senior sales leadership role, alignment on the strategy and then in the same way that, if I'm thinking about going and tackling different revenue motions within that portion of my team, there are going to be areas of specialization whether it be pre-sales, post-sale, pipeline generation, whatever those roles and functions may be. And that counterpart, my senior leader on the other side, ensuring that over time, as there's a more mature organization, they are also building the complementary skill sets across their team to be able to influence these different systems and processes.

And so, you'll see folks where they have Salesforce architects that are specialized in that way because they've got a really mature instance that they're engaging on. You'll have other folks that are going to be much more process oriented and then you'll have folks that are much more delivery oriented, similar to that enablement function. And so, ensuring that you've got the right pieces in place to go and drive against that strategy is the goal.

47:51 DS: When I talk about data as a broad notion, what are the things that jump to your mind as the most useful in a PLG company?

48:04 ST: Well, no matter what, conversion and funnel analysis is the first thing that comes to mind. And where are the pinch points? Where are opportunities to unlock different parts of our funnel?

Now, strictly in a revenue capacity, you're going from on the self-serve side, some level of activation towards your monetization funnel. And on the sales side, it's again a more traditional like “Hey, we've engaged in early conversations” and how do those flow through in terms of the deals that we're closing.

I actually do think the area where I've had over the years to become much more data literate is on the user activation and product engagement metrics, so that I can mine more learnings and understandings of what does it take for someone to activate in a really healthy way. What are the different milestones that someone is engaging with within the product, the time period in which they signed up? What are the indications if someone does something within a one week of activation versus day one of activation? And then, how does that begin to inform the expectations that we would have for what health might look like in a sales-led motion?

I think that the data juxtaposing those two is fascinating because in one, let's take the intent behind self-serving a product. I already know I have a problem of some kind, or a trusted person hopefully invited me into this product or service. And so, I came in with intent. There's a reason I'm here, I'm choosing to engage. Versus, especially if you're going into more expansion oriented play for a sales team, many of those organizations or users that you're trying to pry into, you've got a senior leader or it's you being compelling as the reason why they're discovering and understanding your product for the first time and the expectations on how they're going to activate, on what time frame, and what are the different milestones you want to drive them towards. So, that is a healthy deployment or they're on the right track. Those can be two different things because of the starting place.

And so, understanding the data that goes into that funnel analysis on each is probably one of the first things that jumps to my mind.

50:14 DS: How did you come to understand this, or how did you get a handle on what a healthy rollout looked like or what healthy adoption looked like? And what advice would you have for other folks in a similar position on how to cultivate that?

50:30 ST: Yeah. Loom, as an example, we just ran two funnel meetings weekly. We had a self-serve funnel meeting and then we had a sales-led funnel meeting.

I think the fascinating thing was just seeing the week over week -- we'll call it readouts or documentation – of what we're seeing in aggregate, what are different slices or cohorts of our user base, how does that impact the way in which they're flowing through this funnel at different times. And so, frankly speaking, just the repetition led to education.

Was it a core part of my role to be a member of that meeting? No, not in the moment particularly as I was farther along with building the sales organization, but I felt like it was so important for me to have continued understanding, as well as connectivity with those teams that were driving on that side.

I think on the sales-led side, we would also have folks from growth or product that were assigned to either certain customers, certain customer segments, or certain POCs, depending on where we were. And we used that as a mechanism for them gaining more empathy and understanding of the mechanics of an enterprise sale or a mid-market sale, so that those learnings could also be applied and we could also one, use the subject matter experts as part of our deal cycles because they're product experts, but the second piece as well is just building that connectivity and empathy between the two funnels.

51:59 DS: So, reiterate here, you've got two kinds of processes. And what you said earlier about the maturity of the self-serve particularly at Loom, the self-serve motion before these sales reps came in, before you came in, that was already there. And so, it sounds like that funnel meeting in the self-serve world was happening among the growth team or product team and that's kind of one side of what's happening. And then, you came in and started to really solidify a sales process, so you've now got a separate funnel meeting and these are two parallel things and sounds like what you're suggesting is cross-pollinate, right? Get people from one to go to the other, even if it's not strictly necessary, it's going to help build an understanding of what's happening in the business and it's going to improve both sides.

52:45 ST: Absolutely. And I think it's not just limited to those that are focused on the funnel math or accountable at least to those conversion metrics. If you have PMs that are being brought in because you're making a choice to move up funnel – sorry, move up market – and they need to have a better understanding of what does that actually mean, what are the interactions, we would have our enterprise PMs be a part of those funnel meetings or those forecast calls.

I just think having there be – respectful enough of people's calendar time – but that cross-pollination outside of your executive team, you're going to have your executive weekly meetings or your monthly business reviews where the senior leadership is going to see these different outcomes, these different initiatives, these different projects that are taking place, it's what happening, what's happening at your VP level, what's happening at your director level, what's happening with your management level. And while all of those folks can't be in all of those calls all the time, finding ways that's appropriate for everyone to have context around what's happening and the learnings that are happening across the business, that I would be really intentional on.

53:49 DS: In talking about collaboration across different departments, I'm curious how your perspective on collaboration in general, across a PLG business has changed in going from a peer sales leader to someone who now owns RevOps marketing, other functions as well.

54:10 ST: It's a translation exercise. Everyone wants the same outcome. Everyone wants there to be a successful business.

I think the question is how do we go about doing it. At product-led companies, I will say majority of that translation work, especially when you're in the early innings of a company – I will call it sub 100 employees – there's so much cross-functional overlap that's happening between your R&D teams and your go-to market teams.

Vernacular is so important. People may not know or think about what – when you say ARR, what does that mean? It may go over someone's head. And so, not being afraid to be just like very basic in both asking simple questions – and I think that there's a lot of power in the questions that you're asking.

And so, I've always been really intentional, leading with curiosity for my R&D counterparts so I can get – I'm not technical – some version of understanding and empathy for the challenges and problem set that they're building. And through that, also really taking my time to try and create space for those types of questions and build that common language across the teams as it relates to our go-to market functions.

The piece within – we'll call it the revenue sphere, go-to market world – where it gets really important as well is creating those swim lanes and understanding of where are the different handoff points that are going to happen across these teams, where is it where I'm looking at the leader on the demand gen side of things? Where does their responsibility start? What are the metrics we're hoping that they drive? What are the challenges or opportunities that they're going after? And who's going to be on the other side of that handoff? And making sure there's a ton of connectivity and understanding, particularly between those two handoff points.

You want people to understand the whole funnel. That's important and holistic but getting to the tactics of making sure you've got the folks that are responsible of engaging in really direct ways across your different systems and workflows, that they've got a really strong understanding of what's happening on both sides of that equation.

56:13 DS: Sam, this has been great. Thank you so much for taking this time.

56:17 ST: I’ve enjoyed it, man. It's fun talking about this stuff, so thank you.


Chapters

Selling at PLG Companies

feat. Sam Taylor

Sam Taylor is one of the most experienced Sales leaders in Product-led Growth businesses. In this interview, he shares his experience at Dropbox, Quip, Loom, and Endgame, and discusses how these high-performing PLG companies approached Sales. He discusses the challenges that arise around prioritizing accounts, laying in Enterprise sales, working cross-functionally with Product teams, and using data on product engagement in the sales process.

Chapters

Transcript

0:21 Derek Steer: Sam, great to have you. Thanks so much for joining me today. It would be great if you could start just by introducing yourself and talking in particular about some of the product-led companies where you've worked.

0:42 Sam Taylor: Happy to do it and thanks for having me, Derek. It’s fun. I’ve been on a journey on the product-led side for a number of years. I'd say I really cut my teeth back in 2011 joining the Dropbox team early on. And so, I stumbled my way into being one of the first five sales members of that team and without knowing it at the time, really went through a pretty transformative period as we were figuring out, I think, the early innings of what product-led growth/product-led sales looks like.

I was there for about three and a half years. I joined a small productivity startup called Quip. It was about 20 employees when I joined. We were acquired by Salesforce in the summer of 2016. And so, I'd actually begun my tech career originally at Salesforce, and so going back to the mothership, so to speak, through a different light.

And then most recently, I was leading the global revenue team at Loom, and so was VP of Revenue overseeing our direct sales, customer success, global support, RevOps, and sales assist motions. It really was my first foray in seeing more of the multi-discipline strategy and how do we think about tying those things together.

And then now, three months in, I've joined a company called Endgame as CRO, and we are building a product that is in service of helping these sales teams use product data more elegantly in their motions. That's what I'm up to today.

2:08 DS: So, you've gone from selling in an environment where product data plays a really big component to helping other companies work in that same way. What has that transition been like? I know it's still early.

2:20 ST: It's early but I'm finding a lot of energy where I don't know how long I'll be able to wear this hat, but in essence almost being a voice of the customer and also being a subject matter expert on how these teams think about deploying not only their strategy, the process, the tooling and then ultimately the workflows that they want that motion to take place.

I feel like I'm able to actually wear more of a product hat than expected in the early innings here, which is really fun and energizing. I think also a broad stroke takeaway thus far is everyone does it slightly differently but the themes continue to be the same in terms of the problem areas, and so really fun to get the validation and pattern matching that we're seeing across our customers.

3:02 DS: Let's talk about those themes for a second because a lot of your roles stand in contrast to working at Salesforce, which is not a product-led company. That is a much more traditional top down.

3:13 ST: Let's throw the bodies at it. Yeah.

3:15 DS: Let's throw the bodies, more traditional, I would think. But I'm curious what are the things that all of the PLG companies have going for them or the way that they operate that is different from a company like Salesforce?

3:29 ST: This is not to say that Salesforce is not a systems-oriented entity, absolutely it is. I think on the product-led side, the interesting shift in power internally is that the product or growth function is going to command a lot more of the strategy and a lot more of the sway, if you will, in the decision making at the company.

What I mean specifically around that is if you're in a sales-led enterprise organization, the lifeblood of that company is going to be the revenue that that sales organization is able to drive, so that voice of the customer, the impact of that sales organization, the retention metrics that you see across all the things, that is the driver.

You can find yourself having a lot more centricity around specific customer feedback in those environments versus in a product-led organization, your acquisition strategy is obviously going to be much more around a self-serve orientation both from folks hopping in and exploring your product for the first time and ideally, early monetization movements.

When I think about the breakdown in revenue ownership of what the product-led versus direct sales component of these companies, Dropbox back in the day we're talking 92:8 or even the early innings, it's less than that. At Loom, it would be closer to 85:15 or 90:10 depending on how far we were in our journey there.

And so, it forces a different level of prioritization and also a difficult level of solutioning, which points towards the product side versus the direct hand-to-hand combat that can be sales.

5:11 DS: In a company where the revenue side and that's sales – I imagine in marketing to some extent – but what traditionally you would think of as the org underneath a CRO if it's only contributing – let's call it 15 percent on the high end – what is the role of those organizations? If you had to write a mission statement for those organizations, what would that sound like?

5:39 ST: I think twofold. One, you're on the hook for insights from a customer base and helping drive the insights around one, where is value being driven beyond the individual user. I think depending on the type of product that you're selling, there can be individual user personas, there could be maybe team workspace, org level dynamics that are taking place.

There's only so much that you can really glean from the engagement data that you're seeing across those user behaviors. There's a broader story and impact to how that is being delivered across an entire company. The discovery process that these teams were running, the business cases that they're having to build, those sorts of insights around how that product is driving value at scale, deeply important.

Obviously, you're on the hook for revenue as well. I think that one of the major areas that becomes the decoupling between these motions is many times the folks that are coming in organically, so to speak, into your product and product-led growth orientation are not going to be the same people that are economic buyers or the key decision makers. It's not necessarily, particularly in a large company, the CEO, the VP, the C-suite, that is a part of that user base that you're going to have in a PLG motion. And so, tying those two things together, I think, marrying the bottoms-up momentum that you're building ideally through your product with the tops-down orientation of what it takes to influence and get a deal done, connecting those two different motions together is the mandate and the mission.

7:20 DS: One of the things that seems really challenging about this is understanding what deals require a salesperson to get done. Because I think one of the things that gets associated with product-led growth in a lot of places is self-serve purchasing motion. In a lot of product-led companies, the entry-level products are in fact self-serve and get purchased by swiping a credit card.

I'm curious how you think about setting rep targets or even the department target? How do you figure out what the right amount of revenue to contribute is? Wrapped up in that is attribution too, I'm curious how you think about assigning credit to the sales team when a deal gets done?

8:04 ST: You led with my first instinct which is, it's about swim lanes and attribution to start. I think when I say swim lanes, are you mapping out the different customer journeys that you would expect and the outcomes you would expect? More specifically, we'll take Loom, for example. During my time, there you can have individuals that are gaining a ton of value on Loom. You have folks that are part of a workspace that are gaining a ton of value.

There can be multiple workspaces within a company. If you're a salesperson, you might look at an account that you're working and there's a shotgun of different teams that are leveraging Loom in different ways. Now, unlikely that all of those different workspaces are going to consolidate on their own. It could happen, but unlikely that that would take place.

Second is unlikely that they would self-select into understanding and realizing the path to either upgrading to an enterprise plan, if you're looking at that as your upsell or upgrade path, or are you looking at a more blanketed or broad deployment beyond the organic usage that's taking place.

An example there is great if I'm looking at setting a target for the sales team, we should be having a decent understanding of what is our baseline in terms of the growth rate that we can expect across these smaller self-serve organizations, what is the incremental lift that we are expecting a sales team to drive. And I'd say, as you get more mature in your motion as a team, you can really start to actually look at the net or delta in terms of what the sales organization is driving versus where folks came in at.

I think the funky part about it is this is not a static entity. And so, in many product-led motions, you're going to have, whether it be usage-based, whether it be license-based, there's going to be growth or potentially contraction that's happening on a daily, weekly, monthly basis.

And so, I think a challenge that a lot of companies have experienced and haven't been immune to in my career as well is how do you set the watermark of what an account is worth from a dollar value perspective and then how do you credit or drive attribution for the incremental value that a sales motion is layering on top of that.

I will say in the early innings, we default towards let's get the learnings and let's have sales engaging and we're not going to have there be stringent rules around that incrementality. Once you're getting beyond your first few sets of reps as you're proving out your sales-led motion or layering in product-led sales on top, that's where you start to get it much more defined in terms of the efficiency there.

10:47 DS: Let's talk about how this might work at companies of different scales because what I find interesting about what you just said is with Loom or Dropbox, the products have value from a single player perspective, right? They might be products that you sell into an enterprise and you sell lots and lots of licenses or you sell a lot of usage, they can be valuable as collaboration tools, but they can also be valuable for an individual.

11:14 ST: Yep.

11:15 DS: I'm curious how that dynamic changes when you're selling to a 500 person company versus a 5,000 person company. Is there a material difference or is it really just the same thing no matter how you slice it?

11:29 ST: The complexity comes into the approval and budgeting processes more than anything. Ideally, you're having consistent value that you're able to drive. I think where the early innings of a business case or ROI journey or analysis that you're trying to use to go and justify budget, broader deployment, etc., is that you want to, in an ideal state, be able to prove that there is a network or compounding effect of more players that are in your product engaging the higher value that you are driving. And the more that you can increase the density of those interactions, the higher value that you're seeing.

We would literally, at Dropbox back in the day, have visualizations of the network map of how different users were connected in terms of their sharing connections. It was anonymized so it wasn't about the individual but it would show over time “Hey, you have a much more connected workplace and let's start to attribute value to those connections.”

It's not necessarily a one-to-one in terms of here's a line between two shared folders and that equals a dollar in value, but you start to see that this is truly a collaborative layer as opposed to an individual folder that's sitting on someone's desktop and being able to use that as leverage when you're talking through these business cases.

I think the other piece of this that becomes more front and center is as you go higher and higher into – we'll call it upper mid-market and enterprise type companies, so we'll say 500, 1,000, 5,000 employee companies – you're going to need to be much more strategically aligned. What I mean by that is doing your diligence where you are engaging with an executive, you have an understanding of their business priorities at the company level, and how are you attaching your product and what your product is delivering to those different initiatives.

And that becomes much more of the focal point and much more around make or break, in addition to obviously the bottom-up motion that's taking place at the user level, but ultimately that's what helps in the prioritization and ultimately getting those deals done and budgeted.

13:35 DS: You just said prioritization, and I think it touches on something about product-led businesses that are unique, which is you started off by saying that all this information about Dropbox, for example, the connection is the sharing between one user and another. That was useful as part of the story that you would tell when you were in the sales process.

But what's special that I see is it's also useful in the prospecting motion as well because you have all of that information before you're even engaged in a sales process.

14:04 ST: Yes. The challenge that most of these companies – I'll eventually almost say any of these companies with a large user base – are experiencing is particularly as you have a sales organization, who should you talk to and why? And why is that a good use of your time? And more importantly, why is that a good use and a value-add that you can go and drive with this potential prospect within an account?

I think that that has been, as we've seen the proliferation of tech, the personalization, the how do you get more specificity around why someone should be engaging with you, for what reason, and how you're going to help, is an ever-going challenge. And I think many of us have experienced in our email inboxes that there can be a lack of personalization that falls pretty flat along the way.

The greater the scale on the user base, the greater the insights and the greater the systems that are going to be required to help pinpoint who you should reach out to and why, what's that compelling story.

15:08 DS: One of the biggest challenges that we had with this back when I was at Yammer more than a decade ago was the question of when you should reach out to someone who has not come through the product first.

Dropbox might be the exception where probably everyone or the vast majority of the market has signed up for a Dropbox at some point even just for their personal stuff. But for many folks, Loom still is new in the market, there are a lot of people who haven't used it. When do you go and do a top-down outbound sales motion instead of looking at your list of the people who came up through the product?

15:49 ST: This is where you really have to be structured in capturing your learnings from early customer conversations. And specifically around, we'll take a Loom or Dropbox or Quip, I basically built a career on horizontal productivity tools that can be used in a myriad of ways. While that's amazing because there's so many different ways that you can drive value for an organization, it can become challenging in terms of the pattern matching, particularly in the early days because you're going to get a bunch of different use cases, a bunch of different organizations that are leveraging your technology. And it warrants how do you focus, because if you say that you're everything to everyone, “Are you anything?” would be a framing in question.

16:31 DS: One thing that stands out about that is these horizontal products all have big markets. I'm curious how much that's required. There are exceptions, of course. Figma is a really good example of a market that’s focused on a very particular user type, the designers primarily and then secondarily developers, but they've made a very big business in a product-led way with a particular target.

But I think a lot of the product-led businesses that I can think of are horizontal in part because the markets are just so massive. I'm curious if you think this problem can even be avoided. Because if having a really big market is a critical piece of being a successful product-led company, then everyone who builds around a product-led motion is going to end up with this same kind of challenge of “Hey, who is our audience, really? What do we market and to whom?”

17:27 ST: Yep, and I don't think it's a challenge that can just suddenly be magic wanded to go away. I have found that there becomes an inflection point particularly as you start bolstering your sales organization and your marketing efforts, where you want to be more defined in guiding people towards example use cases, personas that you want to sell to, how are you going to be more targeted.

Really ultimately, that's a narrowing of what are going to be the set of bets that we make, that these two to three personas are the right starting place or where we're going to go deep and ideally prove out a bunch of success, and then begin layering on as we have more and more data to support that that is a repeatable motion.

In the very early innings, you're going to have a lot of spread across these different personas within a company. I think the area where you start to look is who are our healthiest customers, who are the most engaged, and who are actually getting the most value. What can we glean and understand from the dynamics of those teams, how those deals came to fruition, and then from a bottoms up perspective within the user base, actually how did the user acquisition take place and what does health look like, and then really doubling down on how do we go and do our best to repeatedly drive our most successful customers, is the framework that we used in the past.

18:52 DS: It sounds like this is going back to a little bit of what you said earlier about the role of a go-to market organization at a PLG company partially being to get feedback to tie the story of the customer into not just the sales process in the future but also into the product, and to get that mechanism for the product and future development that ultimately is going to drive more adoption.

19:15 ST: Yep, I agree. It's interesting where in the last – we'll call it five, seven years – the concept of a sales assist team is one that has gained a lot of steam.

To kind of define that at a more specific way, having folks that are engaging with your free or paid user base but the self-serve portion of your funnel where you want to have conversations and gain those insights, you want to help them towards buying decision of some kind. These are typically going to be very short cycle, transactional deals that don't really warrant a full quota carrying seller to be working.

In scaled organizations like a Dropbox, those teams actually serve as the feedback mechanism for what should be productized over time, what experiments are working, what are gaps that we have in the different flows on our self-service journey that we think that we can identify with humans, and then productize and become more efficient throughout the way there.

The goal there is how do we frankly just goal people not on revenue and goal people on satisfaction and customer and MPS – call it what you will. And I think that those teams, particularly as you have larger and larger user bases – so call it a Figma, a Miro, a Dropbox at that kind of scale – that's where it becomes really interesting where you decouple the insights at scale from being a responsibility solely of the revenue team or at least your sales organization, because the volume of data points I've seen becomes an issue.

And what I mean by that is if you're a leader on the product side and you're taking a look and you're working with your growth team and you've got millions of users, your data set is massive. Now, you wheel in your mid-market or enterprise sales organization and they're talking about trends that they're seeing across those conversations, those data points are going to be in the tens, if you're in a really solid spot.

It could even be anecdotal in the very early innings, and so that tension between, it's not statistically significant but it doesn't mean that it's not accurate in terms of the reality of what your sellers are experiencing. Figuring out that translation exercise is actually, I think, a really core role of product-led revenue leaders as well to help broker that feedback loop.

21:39 DS: What kind of advice would you give to a leader in a product-led org that is going to start doing more enterprise sales, because that is a somewhat politically fraught challenge?

21:51 ST: If you're a leader that's stepping into a product org that's going up market and enterprise, I recommend that one, you sit down with your peers on the executive team and you define enterprise. I think enterprise is actually a catch-all term and it means so many different things to so many different people. And the follow-up of not only just the term enterprise but the concept of what enterprise readiness means.

Now, I've seen particularly on the product side of the house, there can be moments where enterprise just means it's not self-serve and so we want to have consolidation plays. There can be an enterprise plan. There can be an enterprise-sized customer you're selling to.

And I think really what you're trying to boil down to is what are the ways that we're going to have a common definition and goal around the types of enterprise customers that we want to go and get. An example of a conversation that I'd recommend folks have is, from an industry perspective or looking at your ideal customer profile in the enterprise, who are we going to support, who are we not going to support. An example being like we're not going to support regulated industries off the bat because their security and authentication and all the things, requirements for them to even say yes to your product are going to be way up here and we're not ready from a roadmap perspective to support that.

Now, on the flip side, you have a typical catch-all of something like “Great, we offer SSO and that's our enterprise plan offering” and that's probably not enough for you to have a differentiated experience and go and drive. And so, finding that middle ground between highly regulated or even maybe requests for an on-premise version of your product that you definitely don't want to support in the early days, but having enough meat on the bone around what are you doing to actually drive additional value as well as additional administrative capabilities to go and capture that demand in that segment.

23:44 DS: It's so funny you say defining enterprise as the first thing because it brings me back to my own experiences particularly a mode where to marketing enterprise meant, Let's go get on the gardener magic quadrant because enterprises care about that when they purchase.” Then within Salesforce, we had a very specific number of employees where if you were above that number of employees, you were now an enterprise account.

You may not have necessarily purchased in an enterprise kind of way. In fact, one of the largest customers, the purchaser, was a manager or had a manager title and there wasn't a big political sale that involved lots of departments the way that you would think of enterprise sales traditionally.

It is kind of funny we found that problem over and over again that people will be talking about enterprise coming from different perspectives and mean totally different things.

24:39 ST: It also does shift the way in which you have to think about leveraging the product momentum, if we want to call it that, as you're using that in your sales cycle. Because the farther up the security requirements chain you go, you're really viewed as a threat, like the shadow IT pushback is significant.

And so, it's also been interesting to see culturally within certain companies that you would deem as enterprise. They're not being as warm a reaction to the groundswell of individual users that are signing up for and taking action. I've seen extreme cases where people are actually threatening to shut down or shut off the usage of that, which you absolutely don't want to do.

There's a different level of tact and mentality that, of course, you have to apply in terms of how you're approaching that account, but I also think that's a hefty education for your team internally as a senior leadership team around “No, it's not just rainbows and butterflies that people are heavily engaging with your product, we have to be sensitive to the lens through which other people are looking at that.”

25:46 DS: I'm curious a little bit about when that did happen to you. Because remembering back to my days at Yammer, I would have thought that that would have been common, that getting in through lines of business, having this groundswell and then taking that and going to sell it to a centralized IT department, as Yammer was doing, I would have thought that that would have upset the IT Department because it feels a little shady, you're going behind their back to some degree.

Most of them were just happy to see the engagement statistics. So, the response very often was “Whoa, we don't have other products that get used that much.” And that solves a big problem because shelf wear is a real issue in big enterprises. People pay for stuff and don't use it. On the other hand, Yammer in particular could be used for anything. You could talk about anything, same way you can in Slack, same way you can in any number of products. And so, we had to prove out the value of Yammer over email in some of these cases where it was “Okay, well, we love that it's engaging but is it valuable?”

26:48 ST: Yep. I think the line – and again, to be clear, if this is exception versus rule, I would say the majority of my experience has been what you just described. “We don't want shelf wear. There's clearly a gap in our offering internally, there's a reason why.” I will say the vast majority of folks are approaching that from a place of curiosity and wanting to support as opposed to shutting down.

I do think, depending on the type of product that you have, internal versus externally facing content becomes a hot topic. Whether that be a shared folder for Dropbox, whether that be a Loom that's recording a screen, etc., that can raise flags quickly, particularly for a security team within IT. And so, being sensitive to that and coming from a place of supporting towards a solution versus – let's say Dropbox, the very early playbook, like very earliest innings, I won't say it was like a ransom play but there were so many people using Dropbox. Many of us were approaching those conversations going like “What are you going to do?” You have to buy this thing because your users have spoken and unless that was done tactfully, that can backfire.

27:58 DS: It’s interesting, I once spoke with the sales leader who defined the sales team's role as bypassing objections and effectively said that we wouldn't necessarily need a sales team if everyone just agreed that they should buy our product on its own. The thing that we do is we get past the objections, and it sounds like part of the product-led world is that there's a very specific type of objection that you need to really get honed in on.

I'm hearing two things, really. One being that it's about focus on a particular user type or building out use cases and stories for the different types of personas to whom you will sell. But also, there is a particular focus on security and other similar objections where your objections are less about “Are people using the product?” and more about “How do we wrangle it as an organization and make it work for us?”

28:53 ST: Yeah, and I would also say another framing on that is you're there to help facilitate a buying process, and the buying process at an individual or team level probably doesn't warrant there being a salesperson involved because they can self-serve that flow.

When you think about larger deployments or broader deployments that aren't going to be as organically driven to a conversation we were having earlier, it's just there's a lot more that you have to go through in terms of building consensus, generating buy-in, influencing folks that may or may not be aware of your product offering and its value but getting them to say yes in terms of both prioritization and ultimately budget. That facilitation is where a ton of the work comes in. And I think there's a number of methodologies that are out there that are around like building champions, helping influence within the organization, but also ensuring that you're getting above a particular power line where someone does have decision making and budget authority and the facilitation of mapping that out and helping drive towards hopefully a positive outcome for the sale that you're trying to do is the goal.

30:04 DS: I want to shift gears a little bit and talk about how systems support this motion. What's different about the technical systems that you would use on a sales team or in marketing or the other revenue generating components, what's different in a product-led org versus a more traditional company like Salesforce?

30:24 ST: Yeah, in a product-led org, you’re reacting to “Where are their hotspots within pockets of usage and accounts that you think is worthwhile to prioritize?” The maturity curve for a product-led organization in the early days – let's use the word outbound – you're outbound in my views like you're being proactive trying to go and generate conversations that lead to pipeline and you go and close that aren't coming through a passive or inbound funnel that you currently have.

If someone's raising their hands saying, “I'd love to talk to Derek,” great inbound. “I recognize that Derek's a person that's interesting that I want to go and reach out to and I'm doing that proactively.” I'm doing a version of outbound. That's very different than a cold outbound motion. You're not receiving a cold email, there’s a compelling reason because you're engaged in the product.

Being able to help highlight, identify, and create a structured way to prioritize, what are the accounts, what are the teams, and ultimately what are the people that you want to be engaging with and sell to, that is where the systems get oriented. In a more traditional direct sales organization, you're either going to have someone filled out – I'm being tongue-in-cheek here – but someone filled out a web form and said, “Give me a call. I want to evaluate your widget factory,” great. Or I call you up and say, “Derek, I think you’d love our widgets, you want to talk?” It's a bit more binary and I think the systems component that I see being the intersection between the product data that exists within your user base, the translation exercise of how does that apply to entities. And in this case, an entity is an account, and then within an account there are teams and individuals and ultimately it does boil down to people talking to people. You don't take action on an account, you talk to people, and then how do you help put people in a position to understand trends that are taking place within the user base to help facilitate those conversations.

That's one piece of it. I think as you continue to move up larger and larger deals, we were talking about moving from a mid-market sale, so we'll call it 200 to 1,000 employee companies is a cut that I see a lot of companies is doing – everyone's got a different definition – or even the enterprise where you're getting 5,000 plus. The difference there is going to be the marrying of who's in your product that you want to engage with or at least what are the trends that are happening across that usage, and then pairing that with “Okay, but who are the folks that actually have the decision making authority and being able to go and tell that compelling story to them?”

33:07 DS: One of the things that you left out is you're not really trying to generate additional product usage in other departments, it sounds like, as part of the sales process anyway. You're not going for “Hey, how can we spur product usage in these adjacencies?” It sounds like it's much more focused on the buying dynamics and the budget holders, the people with authority to make a purchase and just lasering it on them.

33:33 ST: I think that depends on the – another spicy word is definition of virality – do you have true virality within your product and can you hinge or expect that there will be growth that takes place?

I think something that I see frequently in terms of the buying dynamic – or excuse me –in terms of the user-based dynamic is that within a team or a department, you can see growth happening organically. So, you have a set of individuals that started with something, now it's within the marketing organization.

Brokering and making the leap over to a sales team or the product organization or engineering or whomever it may be – depending on the product that may or may not be happening given the use cases, how it's being applied etc., the workflows that are being utilized for that product – that's where I do see there being elements from an education perspective where – let's say that we're selling to the COO of a company and that COO oversees operations, marketing, and sales – you may have organic usage that's taking place within your marketing organization, but you haven't really made it on to the op side.

And so, part of that sales process typically is going to be we'd want there to be some kind of proof of concept. We want to prove it out that it would actually be engaging and compelling for a broader set. Let's bring in folks across these different departments and let's set criteria for what success looks like. Let's time box this. Let's go and do this evaluation.

And through that process, you are actually driving more usage because you're opening up new departments or teams that are being exposed to your product. But that should be a time-based thing, and you're driving towards a specific outcome with those actions. And that's something where, as a go-to market and product organization, you need to be well defined around what sorts of deals or what sorts of opportunities do we want to support in that way, just because the resourcing like in essence, you're almost doing the post-sale launch in a pre-sales capacity in order to get people hooked, seeing the value and wanting to say yes to a broader deployment.

35:49 DS: I'm curious whether you think that sales teams at companies with product-led growth motions should compensate their reps on that specific thing, on the expansion from one department to a completely different department that might be totally cold, no sign ups yet in the product at all.

36:08 ST: Again, it goes back to that definition and expectation on virality and if that jump can be made.

I think that I see a number of different ways that people do it. I've been pro compensating on expansion, especially if we have an understanding of what the beginning stages of health look like, we know there's going to be a time component that it takes to grow into that level of health at scale, and how do we then incentivize reps for a certain time window in terms of the growth that's taking place.

The thing that we're actually trying to counteract by doing that, in my experience, is overselling. So, if you're truly a land-and-expand model, you've got the dynamics, you've got the NRR that supports “Hey, let's just go get a bunch of smaller deals” but those deals are hard one, it's tough because you're probably not going to be able to stack up enough of those transactions in a certain time window, whether it be a month, a quarter, a year for how you're compensating those reps.

And so, when you're going from purely self-serve towards your first innings of having a sales team, I've seen that work well. I think once you hit a maturity curve where you have a very good understanding around what would happen over a multi-year period, if those accounts went untouched or they were not sold to and you can start to get a very strong sense of what the true incrementality is for those reps and that you could get much more defined in terms of what you are or what you're not paying out on, and I think really what that hinges on is like the true definition for your business of what net new revenue looks like and what incremental revenue looks like.

37:48 DS: That's interesting. It sounds like what you're suggesting is you could even pay sales people in advance on some of the future growth knowing that that's just a common thing that happens within your customer base, right? If you really do have a product where sharing is a core component such that you definitely expect more usage the following year but…

38:12 ST: I think there's a world in which if you have that level of conviction and understanding of your customer base, that one, from an efficiency perspective, if you're looking at a one-year time horizon of what the true dollar value closed for that sales rep is and your percent payout that you're delivering to that salesperson in terms of commission, that that being weighted in a more sales rep friendly way. So, the efficiency isn't there because you know you're going to make it up in a 12- to 18-month period.

I don't fully believe in compensating on “Hey, someone signed a terms of service” and we hope because they said in a discovery call that they're going to end up doing 200k worth of value when we pay that rep out on day one on the 200k value. I think there does need to be proof that is taking place. And so, that's where I see these time windows around expansion being something more common that I've seen.

39:07 DS: I want to go back to something you said earlier about the usage of product data or it's kind of marrying what's happening within the product with information about a sales process.

I'm curious where the challenges have been in your career in doing this successfully. And are there companies you've worked at that have done it better than others? What does it look like when it's great? And what does it look like on your way to great?

39:36 ST: Yeah, so I've seen multiple flavors of it. I think the most difficult thing to capture is the concept of momentum.

There are going to be things that are constantly shifting in terms of the way that you have multiple players that are playing in this game called your product and some are more active at certain times than not. There may be times where more people are gravitating towards using solutions, there may be times where they're not. And so, how do you capture the right window of opportunity to leverage that or tell a story around that within your sales cycle?

I think in the early days – and I'll use Quip as an example – so Quip was 20 people and I was pleasantly surprised when I joined that they had a really, really robust intranet that allowed us to see workspaces and the delta week over week or day over day of what was happening across a bunch of different parameters.

Now, not ideal because you had to go and pull this information out. It wasn't being surfaced to you proactively. But from the jump, I was able to see week over week trends and you could get a sense of “Oh wow, we've got acceleration that's happening. I should really prioritize engaging with this team, engaging with this account in a positive way or a negative way,” right? “Oh crap, something just fell off the map. Let's go have a conversation and understand that better.”

Outside of that, I think you'll traditionally see that folks will supplement having a version of a BI tool that maybe you have a data team in lockstep with a RevOps team and you're trying to get account level and potentially power user level views of what's happening. And that is initially decoupled from the other sales systems that you're using. An example being Salesforce, where you've got reps that are working leads, they're looking at their accounts, they're doing the reporting, their logging activities in one interface, and then they're going over here to try and understand how they should be prioritizing the day, their week, whatever it may be.

I do think that those BI tools are getting pretty solid. In a more mature organization, you're going to see that be like a tableau. And so, the question then is workflow, and how do you begin to think about more compelling ways to keep focus for your sales organization. I think there's a lot that's out there in terms of statistics around percentage of salespeople's days that are actually spent selling versus researching or doing non-revenue producing activities.

And I think the goal over time is how do you go and get that sense of momentum and prioritization of actions that should be taken and do that in a compelling way.

42:20 DS: You mentioned Quip’s intranet.

42:24 ST: Yep.

42:26 DS: Now, there are products that are available that do some of this as well without having to do a fully bespoke data pipeline and build it into a BI tool and everything, right? There are products like Endgame, that I would imagine would be pretty useful for this sort of thing.

42:41 ST: A hundred percent. And I think that the area there is going to be around one, how do you have a solid understanding of what should or shouldn't be prioritized? And so, combining both what's happening within the sales motions and the outcomes that you've driven, but also what's happening in real time across the customer information or user information. Tying those two things together is challenging.

And the second piece of it is rep workflow. You want to have things that are absolutely driving a ton of value at the systems level, but there still is action prioritization that needs to take place for the selling capacity that you have on your team and making sure that that is an intuitive and elegant experience is the goal as well.

43:21 DS: When you think about setting up these systems, what's the perfect amount of rep engagement with them, in an ideally configured system, that includes Salesforce and maybe something like Endgame, and you've got Outreach or Salesloft, other tools like that?

How much time do you think reps should spend working in those systems, putting in data or searching for things, doing research as opposed to actually selling?

43:51 ST: I don't have an hour breakdown for you, but what I should say is that at the end of the day, a rep should feel like, “I have maximized the number of customer-facing interactions that felt valuable and strategic and that was much more of my time than data entry or searching for data.”

And I think that you mentioned, what does the sliding scale of not-so-great heading towards great,I don't I still don't think that we've completely nailed as an industry what excellent might look like. I think that story is still to be written and part of the journey that I'm currently on. But I do think that bouncing between disparate systems and leaving reps on the hook for tying those different things together in terms of how to prioritize their day and also what story and action they should go and take, is one that is not efficient, whatsoever.

And so, I do think for rep input into this process, having a RevOps team as they're looking at their stack, ensuring that they've got folks that are on the ground that are going to be a part of these workflows day in, day out, weighing in and ensuring that this is actually creating a more streamlined experience for them as opposed to just adding more complexity and more systems that they have to go in. And so, in the same way that you would have your buyer journey, like your customer in this case, is the folks that you're trying to go and have selling in a highly productive way, making sure you're adding to that productivity story as opposed to detracting.

45:25 DS: I'm curious what you think of as the job of RevOps in this PLG world. Because the data team is involved somehow probably, especially if you have a BI tool that's surfacing the product information or if you're getting information from a data warehouse or product database and bringing it into your sales systems.

What should RevOps be doing? As a sales leader, how do you want RevOps to partner with you in that world?

45:52 ST: I've always viewed RevOps as a strategic partner. And what I mean by that is, as we're thinking about themes for a coming year, quarter, whatever the timeframe may be, and particularly through the lens of how do we drive the outcomes that we want and how do we do it, particularly in the last 18 to 24 months in the absolutely most efficient way possible, getting alignment around the strategy. So, what are the themes that we want to go and drive on, but really the delivery of then how do we have the processes and systems that are in service of that and that flow through.

Now, I think, depending on the organization, how it's structured, there are other things that can get tied into a RevOps organization. An example of that being sales enablement. And is RevOps on the hook for actually doing the enablement work themselves? Is there another delivery mechanism? I think that just depends on organizational structure.

But when I think about a senior RevOps leader partnering with someone like myself in a senior sales leadership role, alignment on the strategy and then in the same way that, if I'm thinking about going and tackling different revenue motions within that portion of my team, there are going to be areas of specialization whether it be pre-sales, post-sale, pipeline generation, whatever those roles and functions may be. And that counterpart, my senior leader on the other side, ensuring that over time, as there's a more mature organization, they are also building the complementary skill sets across their team to be able to influence these different systems and processes.

And so, you'll see folks where they have Salesforce architects that are specialized in that way because they've got a really mature instance that they're engaging on. You'll have other folks that are going to be much more process oriented and then you'll have folks that are much more delivery oriented, similar to that enablement function. And so, ensuring that you've got the right pieces in place to go and drive against that strategy is the goal.

47:51 DS: When I talk about data as a broad notion, what are the things that jump to your mind as the most useful in a PLG company?

48:04 ST: Well, no matter what, conversion and funnel analysis is the first thing that comes to mind. And where are the pinch points? Where are opportunities to unlock different parts of our funnel?

Now, strictly in a revenue capacity, you're going from on the self-serve side, some level of activation towards your monetization funnel. And on the sales side, it's again a more traditional like “Hey, we've engaged in early conversations” and how do those flow through in terms of the deals that we're closing.

I actually do think the area where I've had over the years to become much more data literate is on the user activation and product engagement metrics, so that I can mine more learnings and understandings of what does it take for someone to activate in a really healthy way. What are the different milestones that someone is engaging with within the product, the time period in which they signed up? What are the indications if someone does something within a one week of activation versus day one of activation? And then, how does that begin to inform the expectations that we would have for what health might look like in a sales-led motion?

I think that the data juxtaposing those two is fascinating because in one, let's take the intent behind self-serving a product. I already know I have a problem of some kind, or a trusted person hopefully invited me into this product or service. And so, I came in with intent. There's a reason I'm here, I'm choosing to engage. Versus, especially if you're going into more expansion oriented play for a sales team, many of those organizations or users that you're trying to pry into, you've got a senior leader or it's you being compelling as the reason why they're discovering and understanding your product for the first time and the expectations on how they're going to activate, on what time frame, and what are the different milestones you want to drive them towards. So, that is a healthy deployment or they're on the right track. Those can be two different things because of the starting place.

And so, understanding the data that goes into that funnel analysis on each is probably one of the first things that jumps to my mind.

50:14 DS: How did you come to understand this, or how did you get a handle on what a healthy rollout looked like or what healthy adoption looked like? And what advice would you have for other folks in a similar position on how to cultivate that?

50:30 ST: Yeah. Loom, as an example, we just ran two funnel meetings weekly. We had a self-serve funnel meeting and then we had a sales-led funnel meeting.

I think the fascinating thing was just seeing the week over week -- we'll call it readouts or documentation – of what we're seeing in aggregate, what are different slices or cohorts of our user base, how does that impact the way in which they're flowing through this funnel at different times. And so, frankly speaking, just the repetition led to education.

Was it a core part of my role to be a member of that meeting? No, not in the moment particularly as I was farther along with building the sales organization, but I felt like it was so important for me to have continued understanding, as well as connectivity with those teams that were driving on that side.

I think on the sales-led side, we would also have folks from growth or product that were assigned to either certain customers, certain customer segments, or certain POCs, depending on where we were. And we used that as a mechanism for them gaining more empathy and understanding of the mechanics of an enterprise sale or a mid-market sale, so that those learnings could also be applied and we could also one, use the subject matter experts as part of our deal cycles because they're product experts, but the second piece as well is just building that connectivity and empathy between the two funnels.

51:59 DS: So, reiterate here, you've got two kinds of processes. And what you said earlier about the maturity of the self-serve particularly at Loom, the self-serve motion before these sales reps came in, before you came in, that was already there. And so, it sounds like that funnel meeting in the self-serve world was happening among the growth team or product team and that's kind of one side of what's happening. And then, you came in and started to really solidify a sales process, so you've now got a separate funnel meeting and these are two parallel things and sounds like what you're suggesting is cross-pollinate, right? Get people from one to go to the other, even if it's not strictly necessary, it's going to help build an understanding of what's happening in the business and it's going to improve both sides.

52:45 ST: Absolutely. And I think it's not just limited to those that are focused on the funnel math or accountable at least to those conversion metrics. If you have PMs that are being brought in because you're making a choice to move up funnel – sorry, move up market – and they need to have a better understanding of what does that actually mean, what are the interactions, we would have our enterprise PMs be a part of those funnel meetings or those forecast calls.

I just think having there be – respectful enough of people's calendar time – but that cross-pollination outside of your executive team, you're going to have your executive weekly meetings or your monthly business reviews where the senior leadership is going to see these different outcomes, these different initiatives, these different projects that are taking place, it's what happening, what's happening at your VP level, what's happening at your director level, what's happening with your management level. And while all of those folks can't be in all of those calls all the time, finding ways that's appropriate for everyone to have context around what's happening and the learnings that are happening across the business, that I would be really intentional on.

53:49 DS: In talking about collaboration across different departments, I'm curious how your perspective on collaboration in general, across a PLG business has changed in going from a peer sales leader to someone who now owns RevOps marketing, other functions as well.

54:10 ST: It's a translation exercise. Everyone wants the same outcome. Everyone wants there to be a successful business.

I think the question is how do we go about doing it. At product-led companies, I will say majority of that translation work, especially when you're in the early innings of a company – I will call it sub 100 employees – there's so much cross-functional overlap that's happening between your R&D teams and your go-to market teams.

Vernacular is so important. People may not know or think about what – when you say ARR, what does that mean? It may go over someone's head. And so, not being afraid to be just like very basic in both asking simple questions – and I think that there's a lot of power in the questions that you're asking.

And so, I've always been really intentional, leading with curiosity for my R&D counterparts so I can get – I'm not technical – some version of understanding and empathy for the challenges and problem set that they're building. And through that, also really taking my time to try and create space for those types of questions and build that common language across the teams as it relates to our go-to market functions.

The piece within – we'll call it the revenue sphere, go-to market world – where it gets really important as well is creating those swim lanes and understanding of where are the different handoff points that are going to happen across these teams, where is it where I'm looking at the leader on the demand gen side of things? Where does their responsibility start? What are the metrics we're hoping that they drive? What are the challenges or opportunities that they're going after? And who's going to be on the other side of that handoff? And making sure there's a ton of connectivity and understanding, particularly between those two handoff points.

You want people to understand the whole funnel. That's important and holistic but getting to the tactics of making sure you've got the folks that are responsible of engaging in really direct ways across your different systems and workflows, that they've got a really strong understanding of what's happening on both sides of that equation.

56:13 DS: Sam, this has been great. Thank you so much for taking this time.

56:17 ST: I’ve enjoyed it, man. It's fun talking about this stuff, so thank you.


Wanna see what we do next?