The lines between sales-led and product-led growth are blurring. What used to be two distinct sales motions are now complementary to each other.
In this episode we talk to Pete Prowitt—who’s worked for some of the most successful companies in both sales-led and product-led growth.
We talk about:
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Alex Kracov: You started your sales career working at Box, which is more of a traditional sales-led model. Then from there, you went on to work at Quip, Intercom, Loom - all product-led models. I'm curious what you think about is the biggest difference between more of a sales-led versus a product-led model.
Pete Prowitt: I think it really harkens back to this central idea that I've sown from people who are much smarter than myself. It's just really the right tool for the right job. In 2010, after Predictable Revenue came out and Salesforce became the bee's knees in terms of how to change the game in terms of SaaS and building SaaS sales teams and building repeatability at scale, sales-led had to be the tool to get you from A to B for much of the more transactional, more volume-based, more SMB-based business. Because frankly, it was the right tool for the right job.
As technology matures, as teams grow, and as the macroeconomics starts to do things to reward efficiency and efficient growth, things like product-led are pulled forward. It's been really exciting over the past three and a half or four years to see product-led take a bigger piece of the pie, to figure out, hey, this is going to get you not only to $5 mil, $10 mil, $15 mil in ARR. But potentially, product-led could be the biggest catalyst for getting you to $30 or $50 or in some cases, much more than that in ARR.
Alex Kracov: In the actual sales motion itself, what makes sales-led really different than product-led? I know in product-led, that I was just getting dropped into the product itself and starting to play around with it. But how does the mentality of a sales rep change in those two different worlds?
Pete Prowitt: I think this is a fun one, because it's easy to fall into the trap of binary thinking here of just sales-led and product-led as being kind of one or the other either-or, when in reality, a lot of times, it's complimentary. How far can we get with product-led? How can we leverage product as a differentiator to help build a coherent and cohesive buying experience? So just designing for buying. What is the role of product in that? Then at what point is a human the best tool to connect different stakeholders, become multi-threaded deals, and to take complex and nuanced processes, the human processes and to make sure that those are moving in a direction that's going to ultimately increase your chances for closing that deal, closing that revenue?
And so I think that whenever faced with the decision of 'is it better for this to be product-led, or is it better for this to be sales-led,' I was trying to go back into that designing for buying mindset and figure out. If I were buying the software, what would the experience be that I wanted? Is this the right point for a sales rep, for Pete, to jump in and intervene? Is this something where I actually want to do a little bit of exploration to get smart and to figure out how far I can take this on my own?
Alex Kracov: I imagine more complex products that are harder to set up have to be more sales-led, where maybe more SMB can be a little bit more product-led. Is that the right way to think about it?
Pete Prowitt: I think that there's a product complexity layer to it. I think the other thing to think about too, is, if you're building a product in a new space, or you're taking a markedly different approach to an old problem, a lot of times buyers don't know what they don't know. If you divide the world in that Johari window of no known, not unknown, unknown known and unknown unknown, if you're building in a new space, I think that a lot of the AI companies that have come out over the past year, if you're building in a really new, really dynamic and really unknown space, that might actually be a good time for you to intervene earlier in the process to help open up the prospect's eyes in terms of what's possible, and to do a little bit of the challenger sale on traditional thinking earlier.
Alex Kracov: I'd love to talk a little bit about your time at Intercom. I assume, when you joined, you had some level of product market fit. And it was time to scale the business side of things. Can you paint a picture of what Intercom was like when you started?
Pete Prowitt: Yeah, so when I joined Intercom, it was under $2 million revenue with an early sales team, very inbound, very product-led motion. It was just like people loved the product. It was such a fun time to join on the go-to-market side because it was a product that - from an NPS perspective, from a growth perspective, and just from a general virality perspective - was an incredibly buzzy, beloved brand.
I thought that Intercom was a really interesting example where we took an opinionated stance on a space that was well-worn. Like chat wasn't a net new product in that new space. But this idea of personalized communications and customer communications at scale, how to figure out how to be more targeted, and to provide a more bespoke experience. And doing so in a way where we, for the first five, six years, rejected the idea of tickets. Because we just didn't think that that aligned to how humans like to be dealt with. That was really fun because it was opinionated. There were some companies who would opt out early. But for the companies who got it, it was really fun to be a part of pushing thinking forward without being too buzzy on it like a thought leader in the space. So I thought that that was a really interesting lesson, and learning where to be opinionated in product and product roadmap decisions and where that takes you and then, ultimately, where the limitations around that. We revisit a lot of those strongly held opinions earlier on at different points, like change the roadmap.
Alex Kracov: Very cool. I feel like the chat bubble now is super iconic, right? You go to every website, and there's a chat bubble. You go into every product, and there's a chat bubble. But it seems like there was this big education component in Intercom. Yes, it was viral. People really liked it. But you still had to teach people this new way of working with customers. How did you think about building that category and teaching people that, that you were working with?
Pete Prowitt: I think early on, when you're in a new space like that or you're taking a new approach in a well-worn space, you're faced with the challenge of building an ROI story without having completely direct ROI inputs. And so you have to use an example of social proof. You have to use a logical thinking proof. But you also have to tap into this idea of, how can I build the emotional story and resonate with someone on a human level?
If you're on this site, and you got the chat bubble that popped up and it said, "Ask us anything," that's one level of experience. If you're on a site where it's a pricing page, you're specifically looking at b2b versus b2c pricing, and your product in the entertainment space. If you got a chat bubble that said, "Hey, it looks like you're looking for a b2c pricing. You might be in the entertainment space. Here are two examples of companies who have used this in the past. How can we help you?" I think that is maybe bordering on creepy in terms of what you pull in but it's also just relevant. You want to serve somebody up with something relevant and useful. The worst thing you can do - you, as somebody who's worked in good market teams and different startups - the worst thing you can do is not add value. And so I think having that layer of relevance helped us get closer to adding value faster. That was always something I felt good about.
Alex Kracov: I imagine this is where product-led is super powerful, too. Because they can actually see it and play around with it, and see how it impacts them. Yeah, very, very cool. During your time at Intercom, you also transitioned from an IC just to rep selling deals to a manager. I'm curious what that transition was like at a personal level. How did you get yourself ready to be a sales manager?
Pete Prowitt: Yeah, it's funny. I think I've been successful through the different stops in my career. I've felt like I'm good enough at sales to make a career out of it. I also really enjoy sales. Sales is something that's so challenging, and you learn a lot. I had this opportunity to manage a team, to manage a new team that was frankly an experiment. It was like, "We're going to give you this team to manage. We'll give you six months and see if we can prove out some impact." So it's kind of a trial-by-fire type thing. What I was really excited to learn was, one, I liked it. Two, I think it's something that I've gotten better at over time.
I think the challenges of going and being successful as an individual contributor and then moving into management are you kind of like, early on, I fell into the trap of trying to be the super rep in having the answer to everything, where in reality, just because you have a manager title or a leadership title, it doesn't mean that you know everything. Knowing when to phone a friend, knowing when to go into collaborative, and knowing when to-
The hardest thing I think for new managers - it was certainly the case for me - was when to allow somebody to learn through failure. I think that the guidance that one of my mentors told me early on was: when something is too big to let somebody fail, that's when you have to intervene. When you can actually let somebody learn through failure, it can be super, super powerful.
Alex Kracov: Yeah, I definitely experienced that same problem when I was at Lattice. You just see someone messing up. You know how to fix it, but you just need to let it happen. You're just like, "Uh, I want to fix it." But it's so hard.
Alex Kracov: I want to switch gears a little bit and go to your next career stop, which was Loom. And so, from my understanding, a big part of your time at Loom was helping the company move up market. You were tasked with taking this tremendous user growth in a very viral product and turning that into revenue growth. I'm curious just what was that experience like.
Pete Prowitt: Loom was an incredible experience. I was so lucky to be part of it in those early days. When you think about product market fit and virality, Loom was a very special and unique place in my career. There are a number of different factors. One is, it became an incredibly popular video messaging tool on its own. But also, I joined in January of 2020. Then in April of that year is when we entered the pandemic. All of a sudden, asynchronous video messaging, it took on a different level of importance. Signups went from roughly like 2,000 new signups per day to 30, 40, 50 or 60,000 new signups per day for a prolonged period, for a period of months. And so it was just warp speed.
I think some of the early hypotheses we had for building the business, building the up-market motion, dipping our toes in, it got pulled forward. Those are the types of things where it really helped me understand, not only how to be a good sales leader and try to execute in front of against the pipeline in front of you, how to get better learning through deals and testing different plays, but also just the cross functional element. At a product-led growth company like that, you need to be so deeply entrenched with your partners in product, and operations, and engineering. It means that you're really taking a one team-one dream approach. And so having alignment is important in any type of company. But man, building that muscle early at a product-led company has to be a central focus of any revenue leader at those companies.
Alex Kracov: I'm curious what was your relationship like with that product and engineering. Was it basically just - because I assume you're selling? You were trying to sell to bigger companies, and they probably had a lot of team-level features that they needed. Was it basically just communicating with those big companies needed back to the product team? Did you have weekly meetings with them? How did that all kind of work?
Pete Prowitt: We had akin to a weekly staff meeting that would be different across functional leaders. I think when I look back on my time there, a lot of the learnings I took away was, I think, early on in companies and early on as a leader, you're a little bit more into I-want-to-prove-myself mode. I think some of the failure modes that you can fall into, or maybe not exploring, like, hey, is this friction that we're seeing across a subset of deals? Is this something that we want to hold up? You're focused on showing like, "Here's something really cool that we did. Here's the deal that we had to sort of do a Hail Mary on and really pull it in. Here's a Herculean effort."
I think that what I learned during that time was the importance of building great rapport with the leadership team and really and more deeply understanding the challenges that are happening across the company, and figuring out how to work on those holistically. This is a challenge at every leadership team, at every company I've worked with. It's how do you build that empathy and that understanding. So you're really working on the most important problems for you to solve. I don't know if it's fair to say that the typical enterprise sales-led companies versus product-led companies, it's a bigger challenge in one place or another. I know that for every company that I work at after this, really trying to understand product roadmap, trying to understand how engineering tiling works, trying to understand how we make decisions and be a meaningful part of how we make decisions against roadmap, I think that's just part of the evolution of sales leader to revenue leader, go-to-market leader.
Alex Kracov: Yeah, I love one thing you said in there which is telling real customer stories back to the product team. I know. When I was at Lattice, we would do all - I'll have a real customer. We'll interview a real customer or tell our customer a story. Because I feel like the product team can be so caught up in the actual features and the things that are in the app as opposed to the outcomes. They are driving within these organizations. And so those real customer stories can be really helpful in upgrading how the product team thinks about different things.
Pete Prowitt: Some of that is by design, right? As a product leader, you need to care about truly minut details and understand not only what friction customers are feeling today. But what are things that we should potentially challenge their thinking on and really that deep technical detail. I think the other failure mode that I've seen is: at companies that are incredibly sales-led, sometimes you can get in the trap of just like, I need this feature to close this deal. Maybe it's not a broadly shared need. Maybe it's something where another feature would be better served for the business you're building long term.
Trying to avoid just falling into the trap of deal-based anecdote and also just surface level of feature requests to understanding the deeper pain, I think that's one thing that the modern revenue leader or CCO, CRO type needs to be cognizant of. Secondarily, you also will never be better served as a revenue or product leader than getting that direct feedback and experience from your prospects and from your buyers. I think that, as a sales team, there are so many things you can do in terms of revenue roll ups, in terms of problems to be solved, in terms of how you collect and categorize your product and feature requests. But man, it's never going to be as powerful as being on a call or being in the room with the customer and hearing directly from them the things they like, the friction they felt, and what they'd like to see in the future.
Alex Kracov: So you specialized in product-led sales throughout most of your career. We've talked a little bit about the nitty gritty of product-led growth, but I'd love to just spend the next section really getting into all the little details. Product-led growth really starts with the end user. And so I'm curious. How do you take that initial signup, that initial person who just goes into your app and sort of upgrade that into a team-wide or company-wide deployment? What are those steps to make that happen?
Pete Prowitt: I think the first thing - and this is like a little bit more generalized of a playbook - is you want to look at your prospects and lead sources for inbound leads, for outbound leads, and to try to parcel them into different groups. There will likely be some group that's a little bit more transactional, with a lower propensity to pay and, potentially, with a higher propensity to self-serve. Figuring out the characteristics and the shared characteristics of those customers, and then building a true self-serving experience for them, I think, is super important. Then figuring out at what level you want to cap that off and then to pull in your sales-led is so important.
In a previous role, I was able to get to know Yamini Rangan, the CEO of HubSpot, a little bit. One of her secret sauce truisms was: you find the areas where humans are best served to do a job, and then you automate everything else. I think one of the aha moments for me, which is pretty obvious, is that line is going to change over time. So if you're at Series A, you're building your very first self-serving experience, it's probably going to be a more lightweight and less robust service that doesn't work for as many customers as you want, than when it'll be a more mature, a company with more robust offering at a later point.
And so just thinking about that is a sliding scale of, like, if today you can self-serve customers up to 50 full-time employees and then from 50 to 100, or 50 to 300, you want to introduce a sales assist team or a different type of sales-led motion, that's great if that's the right play at that time. Part of your goal is to figure out quarter over quarter have you bumped that up to 75, 150, 300 to allow self-serve to take on a bigger part of your new paid logos and your revenue over time.
Alex Kracov: Got you. Then once you get to a decision-maker or buying committee, how do you think about building the case? What makes someone upgrade and then get that enterprise license?
Pete Prowitt: I always like the concept of graduation. There's some moment in time where - maybe it's in collaborative tools that I've used in the past, there's a tipping point of, if you have five people working in a shared space over the course of a week, maybe that's a good signal for you to say it looks like your organization is getting outsized value from this. Let's talk.
And so bubbling those signals up to your sales team and then figuring out how to work amongst a sales team, whether it's going to be AE-led or a combination of AE and BDR, that becomes the genesis of a sales play. For those companies where it's building consensus and then figuring out what those watershed moments are, I think that's where there's a whole number of tools out there and signals. But just thinking about how to get that signal out to the right team, and then from that signal, starting to develop repeatable plays around how to take pockets of usage and to turn that into more organization-wide deployments. That's kind of the name of the game.
Alex Kracov: Then are you making custom decks and presentations that say, like, "Here's your usage in Loom, in Intercom," and then giving that to your champion to go present to the CFO? How does that work? Because I assume there are so much good usage data that you can use to go convince and say, "Hey, go buy the SSO thing," or, "You need to upgrade."
Pete Prowitt: Yeah, I think that and I know that there's the SSO wall of shame and different things. Sometimes, SSO used to be kind of an Occam's razor to an enterprise upgrade. I feel like today's buyers expect more. There has to be an additional level of service, of SLA, of functionality. It's something that they deem to be valuable to really spur that organization-wide deployment. And so it's hard to generalize across different tools, industries, things like that.
The one thing that I would say is: for anybody who's looking to do some version of this play - where it's to take pockets of usage and then to turn that into organization-wide or company-wide deployments - it's really important to talk to your initial set of users and understand what are the problems that they want to solve, what sort of impact do they see, what do they wish they could see, and bake that in to something that would be a more org-level priority.
So if you have a group of product managers who are using a video messaging tool as a means to share rich context and feedback across time zones, that could be something that is mapped to a new product release that has outsized organizational impact. From there, can really tie into something where your VP of Product who has access to budget, who has this company-level priority, would be more interested to invest in a broader deployment versus just saying, "You have five users. Here's an SSO upgrade. Let's get an additional 400."
Alex Kracov: I remember there's a very funny website of the SSO Wall of Shame that the old IT guy at Lattice sent me. That was like all the companies that just make you upgrade for the SSO. It's a funny thing, and I'm glad that trend has-
Pete Prowitt: The person who told you, that person at Lattice in previous, I had seen that same website from him. It was great.
Alex Kracov: Yeah, he's the best. Hello, Frank. Shout out to Frank. One thing I struggle with is the fake champion. It's like there's this end user who promises you the world. They're like, "We'll help you get into the organization." But they don't really have a lot of sway. I'm curious. How do you deal with that dynamic? How do you approach with multi-threading and making sure you're talking to the right person at the company at the customer side of things?
Pete Prowitt: Yeah, this is a great one. This is an age-old problem. There are different sales methodologies and ways to characterize it. There's one that's stuck with me. It's this idea of champions versus coaches. Both are valuable, but one is going to get you farther across the deal. Identifying who's who early is so important.
One of the concepts that we really preach on our team is testing your champions early. It's one thing to ask the question, do you have my authority? A more artful version on that. But to actually test and see through functional validation, through technical validation, through talking, through, "Hey, what past vendors have been successful here? What were the behaviors they saw? How did you shepherd them through?" You start to get a sense of, is this somebody who can actually drive me forward, or do I have to figure out another area of the company to multithread into? Man, I cannot emphasize the importance of testing your champions early and trying to validate. Because the risk you run, particularly in a tough macro-economic environment like 2023, is you spend a couple months on a deal that you think is going to get you to your number. It's just a lot of wasted calories on something that pushes or ultimately doesn't close last because the person that you're dependent on or a group of people you're dependent on can't ultimately get you to it.
One of the things that has been emphasized in recent months is, you really want to get a sense of your prospect's business model and how they make money, profit margins. This is easier to do when you're selling to publicly-traded companies, where you can go into different reports that are filed. But if you can get a sense of it's just a business model that appears to be growing, that appears to be viable, you can have a higher level of confidence in those deals closing. Because dollars maybe aren't as hard won.
In businesses that are suffering outsize right now, you run the risk of just a new CFO or a new initiative coming in. Even if you have the right buyer, spending freeze, it's just happened overnight. Trying to go through your pipeline and fine-tooth comb and say like, this is a business that's growing. This is a business where it's not easy money versus hard money. But you're not going to be under the same level of rigor if you're in a business that's thriving versus a business that's going through a tougher patch.
Alex Kracov: You touched on the macro and how things are a little bit different now in 2023. I think it started there. You have the benefit of perspective, right? You've been doing this for a while. We're hearing the good times and then the zero-interest rate environment. I'm curious. Are there other trends you're seeing in what makes selling now different than the early days of Intercom or even before that?
Pete Prowitt: Yeah, I remember when I first joined Box, it was coming off of a really tough macro with the 2008-2009 financial slowdown and just trying to get back. One of the things that at the time felt like a real challenge when I look back, and I'm very thankful for, was business cases were hard won. Deals were hard won. ROI was a part of every conversation, hard stuff. I think that in a tough macro, the idea of ROI is always important. But it is so important to establish early to understand how does your service make or save someone money. Then being able to flesh that out early, come to mutual agreement, and then every single conversation, touchpoint and technical validation that you do, has to map back to that why and sort of the how do we make or save your money.
I talked to a CRO who had sold his company service to a FANG type company a year ago. It was a 100k deal. It required two signatures. It was a relatively fast-deal cycle. This year, to renew it at the exact same level after a relatively successful first year, it required 17 signatures. And so just little things like that. How many people are involved in the buying process, and what's the level of scrutiny over each dollar? It's a small anecdote to me, but it's just a reminder of every single thing you can do to run a tighter sales process and to harken back to a strong ROI case is the best way to safeguard yourself away from losing deals, missing targets, et cetera.
Alex Kracov: How do you think about building that ROI case? Because when I tried to do this in the past, it feels like I'm always - I don't know. I'm building some ROI calculator in an Excel Google Sheet and making up these metrics and stuff. What's always hard about it is I don't know their business that well. I don't have how much their sales reps cost. And so I don't know. What's this balance between? How do you do that? Do you just make up numbers? Do you ask them for inputs? What do you think is the best way to build that ROI case?
Pete Prowitt: It's easier to do in some spaces, in some industries than others. I think that the key - particularly when you're in a newish space, or you're taking a new approach where ROI isn't just generally accepted - is that really collaborative feedback and making sure that you get mutual agreement, mutual buy in at every step.
If you can get to the space of saying, "Hey, I'm going to save you 100 developer hours per month. From what I see, you have 20 developers on LinkedIn. I'm ballparking what their annual salaries are. Based on what you told me before, it sounds like you're spending x number of hours working on these projects. Is this accurate?" At some point, if you're taking those thoughtful approaches and you're getting really collaborative, people will share. Like, this a real problem I'm feeling, things like that. They can also say, "I don't think 100 is real. Maybe you can only save me 50." But the key is, if you're going through that ROI calculator, if you're just depending on the ROI calculator that somebody puts on a marketing website with a bunch of inputs, I think that is usually met with a level of skepticism, where if you can go through that mutual validation process, you're a little bit more likely to come up with something that is defensible.
Alex Kracov: Very interesting. I'd love to switch gears and talk a little bit about you personally and your transition into a revenue leader. Over your career - we talked about this before - you went from an IC to a manager. Then at Rewatch and now at Stytch, you're a VP. You're VP of revenue. And so I'm curious. What is that transition like? What do you think is the biggest difference between being a revenue leader, sort of at the VP level, versus being a manager on a sales team?
Pete Prowitt: I think that at each stop - I've just been really lucky to work at great companies who've been funded by great VCs. I get to work with really smart people. At each stop, the key is really trying to figure out what is your special sauce that you bring to the table. What is your superpower? And how does that tie into something that is important to the company right now?
I think with each kind of place that I've worked, I've developed a different skill set. At Box, for me, it was really learning the enterprise sales book. At Intercom, it was really trying to figure out like, hey, for an early product-led growth company, how do you build a go-to-market team? How do you build a sales team that is truly complementary and not cannibalizing self-serve, adding value, helping move up market, and driving that dollar retention? At these different places, you learn how to tap into your background and your skill set and figure out how to have the most impact.
I think that the thing that I love most - I've discovered this over the past couple of years - is when you're building zero-to-one or one-to-five teams, everything you do has outsize impact. Everything you do, from hiring a person, setting a culture, setting a performance bar, reinforcing that performance bar, it sets the table for the next 3, 6, 18 months. I think that it's a combination of the scrappiness and just figuring out how to get things done, doing things that don't scale. But also, just trying to look around the corner and think if I am setting this performance bar now and we're anchored at this level, is this going to be something that helps us 18 months from now? Is this the right kind of standard to set today? That's something I'm always thinking about. I'm always trying to figure out how can we make sure that we're setting ourselves up for the better next 12, 24 months.
Alex Kracov: It's like the first 90 days of leading a revenue team is just so important, especially when you come in from the outside. There's just a lot of trust you need to build in both directions, with the sales reps on your team and with the leadership team. And so, how do you think about building trust? Is it getting quick wins? How do you think about coming in and just making an impact right away?
Pete Prowitt: It has definitely evolved over time. I think that a failure mode that you see sometimes, and I fall into in the past, is you want to come in and just hit the ball at a park right away. Sometimes you can be more prescriptive than really trying to understand what are the problems that we're facing today, how the different teams interact. If we take as a use of systems thinking approach to this, what are some of the functions and dysfunctions that we really want to lean into over the next quarter or quarters? I also think that, depending on the stage of the company you join, you don't want to get too strategic and far away from deals and deal execution.
The worst thing that you can do particularly in a year like this is to drop the bomb execution. Every CRO I know, every VP of sales I know has been more deal-level focused this year than they have in the past 10. I think that's because there's a real opportunity cost. Pipeline is hard won today. It's sort of like trying to balance the organization's priorities and your strengths and skill sets at the time, but also just knowing what's going to be most important, trying to be that chameleon. For me, right now, I'm toggling a little bit further back into deals, making sure that of the pipeline that we have, that we're executing as best as we can. I'm constantly learning what plays work, what don't. I think that that's more of a broadly-shared trend.
Alex Kracov: Yeah, let's talk about that, your current role at Stytch. Stycth is - correct me if I'm wrong - an API for authentication and identities. You sell primarily to developers. That's a little bit different than what you've done in the past. And so I'm curious. How do you approach selling to developers? I can't imagine they enjoy talking to salespeople too much.
Pete Prowitt: I don't know. I think I'm pretty fun to talk to.
Alex Kracov: Yeah, you are.
Pete Prowitt: You are absolutely right. I think for Stytch, which is an API-first and developer-first platform for building authentication that supports not only password base but a lot of passwordless authentication flows, what we're doing is we're taking this problem that people have solved in a very straightforward way, with passwords being the backbone for authentication for the past 50 years, and really turning it on its head in some ways and figuring out how do we become the bridge to passwordless? How do you reduce friction on the internet for your users? How do we make sure that people are seeing the value of your product and getting to those aha milestone moments as fast as possible?
What we found is, over the past year, we have a really technical buyer on deals where there's not a VP of engineering or there's not a CTO. It becomes very hard for us to sort of sequester the engineering resources we need to test to validate, and to get real feedback on what migration would look like, and how the solution design authentication. And so, for me, the challenge is that this is the most technical product I've sold, and it's also a really technical buyer.
One of the things that I've learned over the past year is figuring out an outsize role of solutions engineering having really technical counterparts, and then figuring out the interplay between more process-focused account executives and sales professionals, and then where to plug in those solutions engineers. As somebody who's worked in partner selling with solution engineers at many different steps along the way, I have never appreciated that team more than today. Because I think we got to this point where the AE and the sales professional becomes responsible for the what. Why are we doing this? What are we looking to do? Then the solutions engineer becomes the how. It just created this really powerful dynamic that's led us to bigger deals, better deals, and to more traction as we start to find our groove on that front.
Alex Kracov: How does that collaboration work? Because you have the AE. You have the solutions engineer, and then you obviously have the customer who's a developer. Are you sort of all collaborating in a sales proof of concept document? Do you have a shared Slack channel? Because there must be just a lot of next steps you're sharing or to-dos and things. There's just a lot of alignment that needs to happen. And so I'm curious what that looks like practically.
Pete Prowitt: Totally. Well, I think most AES have heard some version of you become the quarterback of your deals type speech. But in a deal like this where it's technical stakeholders, it's technical leaders, then it's really important to meet your individual contributor developers on the right level and then to figure out how to solve problems for both of them over the course of a deal. There's a lot of coordination that happens internally. And so that'll be an AE working not only with their solutions engineer, but potentially interacting with folks on our product team, our engineering team to talk through roadmap, talk through how to proof of concept different things, trying to figure out, hey, if we advise in this direction, is that going to create complexity later on?
And so it's a lot of Slack channels. We'll have internal Slack channels for customers. We'll have external Slack channels with customers. It's figuring out like, what are the best ways for us to to drive that internal collaboration? So that at each call, we're coming in not only with a well-prepared presentation and well-prepared demo, but also really thoughtful and bespoke solutions designed for customers that are going to help them solve today problems and future proof them. When you're selling a core infrastructure, the future-proof piece is so important. Because nobody wants to rip out authentication more than once every 5, 10 years. So proving out that you're going to be the best long-term partner is so key.
Alex Kracov: Yeah, it puts more emphasis just on those technical proof of concepts. The good thing about Stytch is, once it's in there, they're probably very unlikely to turn. It's a very sticky product, which is awesome.
Pete Prowitt: We love to do our job. But yeah, that's the fun part of it.
Alex Kracov: I'd love to end on a fun note. I think before business, you are a basketball player, right? You played for Stanford's basketball team. And yeah, I don't know. I'm curious if there's any lessons you learned from sports that you apply to sales. Anything about that experience make you a better leader?
Pete Prowitt: Yeah, I feel like I can fall into the stereotypical former athlete goes into sales model. But for me, I really don't feel comfortable unless I'm in that team environment - in a team environment where you're pushing yourself really hard, but you're also pushing each other. I remember having very candid conversations with my coaches, with my point guards. Sometimes my point guards didn't give me the ball on the right block in the exact place I liked. I would have very candid conversations with them. But there's something that's so comforting and functional around a team that is holding each other accountable, a team where you really feel like you win or lose together, and a structure where you put a lot of accountability and emphasis on your own performance. For me, that was such a natural transition into sales.
After basketball, I had a chance to play briefly overseas. I had a couple of different jobs. I was a speechwriter at an international organization, which is kind of fun, as an investment banker very briefly in Boston during one of the snowpocalypse. But I didn't really find that environment that was a proxy for what team sports was, until I got into sales. For the past 12, 13 years, it's been a really happy place.
Alex Kracov: I think that the funnest part about sales is that team rah rah sort of environment. I started my career at Yelp. That was definitely what it felt like. I feel like with the pandemic and remote work, we've maybe lost a little bit about that. But maybe the pendulum is swinging back, so we'll see. We'll see what happens. Thank you so much, Pete. This was a wonderful conversation. If people want to follow up with you, ask questions, promote yourself. Where the best place? LinkedIn, Twitter?
Pete Prowitt: LinkedIn is a great place. If you want to drop me a note, I'm just pete@stytch.com. Thanks so much for the conversation. It's really fun.
Alex Kracov: Thanks so much, Pete.
Pete Prowitt is the Head of Revenue at Stytch.
Pete's sales career started with a more traditional sales model at Box.
Then, he was an early sales hire at Quip, which helped pioneer the PLG model. He then joined Intercom as one of the first five sales reps—helping grow Intercom from $1m to $140m in revenue over 5 years.
Next, Pete joined as the first sales leader at Loom, leading sales from $1m to $7m ARR. After Loom, he led the revenue team at Rewatch before taking on his current role at Stytch.
Before working in sales, Pete had stints as a speechwriter and as an investment banker. Prior to that, he played basketball at Stanford and in Germany.
The lines between sales-led and product-led growth are blurring. What used to be two distinct sales motions are now complementary to each other.
In this episode we talk to Pete Prowitt—who’s worked for some of the most successful companies in both sales-led and product-led growth.
We talk about:
Enjoy the show!
Alex Kracov: You started your sales career working at Box, which is more of a traditional sales-led model. Then from there, you went on to work at Quip, Intercom, Loom - all product-led models. I'm curious what you think about is the biggest difference between more of a sales-led versus a product-led model.
Pete Prowitt: I think it really harkens back to this central idea that I've sown from people who are much smarter than myself. It's just really the right tool for the right job. In 2010, after Predictable Revenue came out and Salesforce became the bee's knees in terms of how to change the game in terms of SaaS and building SaaS sales teams and building repeatability at scale, sales-led had to be the tool to get you from A to B for much of the more transactional, more volume-based, more SMB-based business. Because frankly, it was the right tool for the right job.
As technology matures, as teams grow, and as the macroeconomics starts to do things to reward efficiency and efficient growth, things like product-led are pulled forward. It's been really exciting over the past three and a half or four years to see product-led take a bigger piece of the pie, to figure out, hey, this is going to get you not only to $5 mil, $10 mil, $15 mil in ARR. But potentially, product-led could be the biggest catalyst for getting you to $30 or $50 or in some cases, much more than that in ARR.
Alex Kracov: In the actual sales motion itself, what makes sales-led really different than product-led? I know in product-led, that I was just getting dropped into the product itself and starting to play around with it. But how does the mentality of a sales rep change in those two different worlds?
Pete Prowitt: I think this is a fun one, because it's easy to fall into the trap of binary thinking here of just sales-led and product-led as being kind of one or the other either-or, when in reality, a lot of times, it's complimentary. How far can we get with product-led? How can we leverage product as a differentiator to help build a coherent and cohesive buying experience? So just designing for buying. What is the role of product in that? Then at what point is a human the best tool to connect different stakeholders, become multi-threaded deals, and to take complex and nuanced processes, the human processes and to make sure that those are moving in a direction that's going to ultimately increase your chances for closing that deal, closing that revenue?
And so I think that whenever faced with the decision of 'is it better for this to be product-led, or is it better for this to be sales-led,' I was trying to go back into that designing for buying mindset and figure out. If I were buying the software, what would the experience be that I wanted? Is this the right point for a sales rep, for Pete, to jump in and intervene? Is this something where I actually want to do a little bit of exploration to get smart and to figure out how far I can take this on my own?
Alex Kracov: I imagine more complex products that are harder to set up have to be more sales-led, where maybe more SMB can be a little bit more product-led. Is that the right way to think about it?
Pete Prowitt: I think that there's a product complexity layer to it. I think the other thing to think about too, is, if you're building a product in a new space, or you're taking a markedly different approach to an old problem, a lot of times buyers don't know what they don't know. If you divide the world in that Johari window of no known, not unknown, unknown known and unknown unknown, if you're building in a new space, I think that a lot of the AI companies that have come out over the past year, if you're building in a really new, really dynamic and really unknown space, that might actually be a good time for you to intervene earlier in the process to help open up the prospect's eyes in terms of what's possible, and to do a little bit of the challenger sale on traditional thinking earlier.
Alex Kracov: I'd love to talk a little bit about your time at Intercom. I assume, when you joined, you had some level of product market fit. And it was time to scale the business side of things. Can you paint a picture of what Intercom was like when you started?
Pete Prowitt: Yeah, so when I joined Intercom, it was under $2 million revenue with an early sales team, very inbound, very product-led motion. It was just like people loved the product. It was such a fun time to join on the go-to-market side because it was a product that - from an NPS perspective, from a growth perspective, and just from a general virality perspective - was an incredibly buzzy, beloved brand.
I thought that Intercom was a really interesting example where we took an opinionated stance on a space that was well-worn. Like chat wasn't a net new product in that new space. But this idea of personalized communications and customer communications at scale, how to figure out how to be more targeted, and to provide a more bespoke experience. And doing so in a way where we, for the first five, six years, rejected the idea of tickets. Because we just didn't think that that aligned to how humans like to be dealt with. That was really fun because it was opinionated. There were some companies who would opt out early. But for the companies who got it, it was really fun to be a part of pushing thinking forward without being too buzzy on it like a thought leader in the space. So I thought that that was a really interesting lesson, and learning where to be opinionated in product and product roadmap decisions and where that takes you and then, ultimately, where the limitations around that. We revisit a lot of those strongly held opinions earlier on at different points, like change the roadmap.
Alex Kracov: Very cool. I feel like the chat bubble now is super iconic, right? You go to every website, and there's a chat bubble. You go into every product, and there's a chat bubble. But it seems like there was this big education component in Intercom. Yes, it was viral. People really liked it. But you still had to teach people this new way of working with customers. How did you think about building that category and teaching people that, that you were working with?
Pete Prowitt: I think early on, when you're in a new space like that or you're taking a new approach in a well-worn space, you're faced with the challenge of building an ROI story without having completely direct ROI inputs. And so you have to use an example of social proof. You have to use a logical thinking proof. But you also have to tap into this idea of, how can I build the emotional story and resonate with someone on a human level?
If you're on this site, and you got the chat bubble that popped up and it said, "Ask us anything," that's one level of experience. If you're on a site where it's a pricing page, you're specifically looking at b2b versus b2c pricing, and your product in the entertainment space. If you got a chat bubble that said, "Hey, it looks like you're looking for a b2c pricing. You might be in the entertainment space. Here are two examples of companies who have used this in the past. How can we help you?" I think that is maybe bordering on creepy in terms of what you pull in but it's also just relevant. You want to serve somebody up with something relevant and useful. The worst thing you can do - you, as somebody who's worked in good market teams and different startups - the worst thing you can do is not add value. And so I think having that layer of relevance helped us get closer to adding value faster. That was always something I felt good about.
Alex Kracov: I imagine this is where product-led is super powerful, too. Because they can actually see it and play around with it, and see how it impacts them. Yeah, very, very cool. During your time at Intercom, you also transitioned from an IC just to rep selling deals to a manager. I'm curious what that transition was like at a personal level. How did you get yourself ready to be a sales manager?
Pete Prowitt: Yeah, it's funny. I think I've been successful through the different stops in my career. I've felt like I'm good enough at sales to make a career out of it. I also really enjoy sales. Sales is something that's so challenging, and you learn a lot. I had this opportunity to manage a team, to manage a new team that was frankly an experiment. It was like, "We're going to give you this team to manage. We'll give you six months and see if we can prove out some impact." So it's kind of a trial-by-fire type thing. What I was really excited to learn was, one, I liked it. Two, I think it's something that I've gotten better at over time.
I think the challenges of going and being successful as an individual contributor and then moving into management are you kind of like, early on, I fell into the trap of trying to be the super rep in having the answer to everything, where in reality, just because you have a manager title or a leadership title, it doesn't mean that you know everything. Knowing when to phone a friend, knowing when to go into collaborative, and knowing when to-
The hardest thing I think for new managers - it was certainly the case for me - was when to allow somebody to learn through failure. I think that the guidance that one of my mentors told me early on was: when something is too big to let somebody fail, that's when you have to intervene. When you can actually let somebody learn through failure, it can be super, super powerful.
Alex Kracov: Yeah, I definitely experienced that same problem when I was at Lattice. You just see someone messing up. You know how to fix it, but you just need to let it happen. You're just like, "Uh, I want to fix it." But it's so hard.
Alex Kracov: I want to switch gears a little bit and go to your next career stop, which was Loom. And so, from my understanding, a big part of your time at Loom was helping the company move up market. You were tasked with taking this tremendous user growth in a very viral product and turning that into revenue growth. I'm curious just what was that experience like.
Pete Prowitt: Loom was an incredible experience. I was so lucky to be part of it in those early days. When you think about product market fit and virality, Loom was a very special and unique place in my career. There are a number of different factors. One is, it became an incredibly popular video messaging tool on its own. But also, I joined in January of 2020. Then in April of that year is when we entered the pandemic. All of a sudden, asynchronous video messaging, it took on a different level of importance. Signups went from roughly like 2,000 new signups per day to 30, 40, 50 or 60,000 new signups per day for a prolonged period, for a period of months. And so it was just warp speed.
I think some of the early hypotheses we had for building the business, building the up-market motion, dipping our toes in, it got pulled forward. Those are the types of things where it really helped me understand, not only how to be a good sales leader and try to execute in front of against the pipeline in front of you, how to get better learning through deals and testing different plays, but also just the cross functional element. At a product-led growth company like that, you need to be so deeply entrenched with your partners in product, and operations, and engineering. It means that you're really taking a one team-one dream approach. And so having alignment is important in any type of company. But man, building that muscle early at a product-led company has to be a central focus of any revenue leader at those companies.
Alex Kracov: I'm curious what was your relationship like with that product and engineering. Was it basically just - because I assume you're selling? You were trying to sell to bigger companies, and they probably had a lot of team-level features that they needed. Was it basically just communicating with those big companies needed back to the product team? Did you have weekly meetings with them? How did that all kind of work?
Pete Prowitt: We had akin to a weekly staff meeting that would be different across functional leaders. I think when I look back on my time there, a lot of the learnings I took away was, I think, early on in companies and early on as a leader, you're a little bit more into I-want-to-prove-myself mode. I think some of the failure modes that you can fall into, or maybe not exploring, like, hey, is this friction that we're seeing across a subset of deals? Is this something that we want to hold up? You're focused on showing like, "Here's something really cool that we did. Here's the deal that we had to sort of do a Hail Mary on and really pull it in. Here's a Herculean effort."
I think that what I learned during that time was the importance of building great rapport with the leadership team and really and more deeply understanding the challenges that are happening across the company, and figuring out how to work on those holistically. This is a challenge at every leadership team, at every company I've worked with. It's how do you build that empathy and that understanding. So you're really working on the most important problems for you to solve. I don't know if it's fair to say that the typical enterprise sales-led companies versus product-led companies, it's a bigger challenge in one place or another. I know that for every company that I work at after this, really trying to understand product roadmap, trying to understand how engineering tiling works, trying to understand how we make decisions and be a meaningful part of how we make decisions against roadmap, I think that's just part of the evolution of sales leader to revenue leader, go-to-market leader.
Alex Kracov: Yeah, I love one thing you said in there which is telling real customer stories back to the product team. I know. When I was at Lattice, we would do all - I'll have a real customer. We'll interview a real customer or tell our customer a story. Because I feel like the product team can be so caught up in the actual features and the things that are in the app as opposed to the outcomes. They are driving within these organizations. And so those real customer stories can be really helpful in upgrading how the product team thinks about different things.
Pete Prowitt: Some of that is by design, right? As a product leader, you need to care about truly minut details and understand not only what friction customers are feeling today. But what are things that we should potentially challenge their thinking on and really that deep technical detail. I think the other failure mode that I've seen is: at companies that are incredibly sales-led, sometimes you can get in the trap of just like, I need this feature to close this deal. Maybe it's not a broadly shared need. Maybe it's something where another feature would be better served for the business you're building long term.
Trying to avoid just falling into the trap of deal-based anecdote and also just surface level of feature requests to understanding the deeper pain, I think that's one thing that the modern revenue leader or CCO, CRO type needs to be cognizant of. Secondarily, you also will never be better served as a revenue or product leader than getting that direct feedback and experience from your prospects and from your buyers. I think that, as a sales team, there are so many things you can do in terms of revenue roll ups, in terms of problems to be solved, in terms of how you collect and categorize your product and feature requests. But man, it's never going to be as powerful as being on a call or being in the room with the customer and hearing directly from them the things they like, the friction they felt, and what they'd like to see in the future.
Alex Kracov: So you specialized in product-led sales throughout most of your career. We've talked a little bit about the nitty gritty of product-led growth, but I'd love to just spend the next section really getting into all the little details. Product-led growth really starts with the end user. And so I'm curious. How do you take that initial signup, that initial person who just goes into your app and sort of upgrade that into a team-wide or company-wide deployment? What are those steps to make that happen?
Pete Prowitt: I think the first thing - and this is like a little bit more generalized of a playbook - is you want to look at your prospects and lead sources for inbound leads, for outbound leads, and to try to parcel them into different groups. There will likely be some group that's a little bit more transactional, with a lower propensity to pay and, potentially, with a higher propensity to self-serve. Figuring out the characteristics and the shared characteristics of those customers, and then building a true self-serving experience for them, I think, is super important. Then figuring out at what level you want to cap that off and then to pull in your sales-led is so important.
In a previous role, I was able to get to know Yamini Rangan, the CEO of HubSpot, a little bit. One of her secret sauce truisms was: you find the areas where humans are best served to do a job, and then you automate everything else. I think one of the aha moments for me, which is pretty obvious, is that line is going to change over time. So if you're at Series A, you're building your very first self-serving experience, it's probably going to be a more lightweight and less robust service that doesn't work for as many customers as you want, than when it'll be a more mature, a company with more robust offering at a later point.
And so just thinking about that is a sliding scale of, like, if today you can self-serve customers up to 50 full-time employees and then from 50 to 100, or 50 to 300, you want to introduce a sales assist team or a different type of sales-led motion, that's great if that's the right play at that time. Part of your goal is to figure out quarter over quarter have you bumped that up to 75, 150, 300 to allow self-serve to take on a bigger part of your new paid logos and your revenue over time.
Alex Kracov: Got you. Then once you get to a decision-maker or buying committee, how do you think about building the case? What makes someone upgrade and then get that enterprise license?
Pete Prowitt: I always like the concept of graduation. There's some moment in time where - maybe it's in collaborative tools that I've used in the past, there's a tipping point of, if you have five people working in a shared space over the course of a week, maybe that's a good signal for you to say it looks like your organization is getting outsized value from this. Let's talk.
And so bubbling those signals up to your sales team and then figuring out how to work amongst a sales team, whether it's going to be AE-led or a combination of AE and BDR, that becomes the genesis of a sales play. For those companies where it's building consensus and then figuring out what those watershed moments are, I think that's where there's a whole number of tools out there and signals. But just thinking about how to get that signal out to the right team, and then from that signal, starting to develop repeatable plays around how to take pockets of usage and to turn that into more organization-wide deployments. That's kind of the name of the game.
Alex Kracov: Then are you making custom decks and presentations that say, like, "Here's your usage in Loom, in Intercom," and then giving that to your champion to go present to the CFO? How does that work? Because I assume there are so much good usage data that you can use to go convince and say, "Hey, go buy the SSO thing," or, "You need to upgrade."
Pete Prowitt: Yeah, I think that and I know that there's the SSO wall of shame and different things. Sometimes, SSO used to be kind of an Occam's razor to an enterprise upgrade. I feel like today's buyers expect more. There has to be an additional level of service, of SLA, of functionality. It's something that they deem to be valuable to really spur that organization-wide deployment. And so it's hard to generalize across different tools, industries, things like that.
The one thing that I would say is: for anybody who's looking to do some version of this play - where it's to take pockets of usage and then to turn that into organization-wide or company-wide deployments - it's really important to talk to your initial set of users and understand what are the problems that they want to solve, what sort of impact do they see, what do they wish they could see, and bake that in to something that would be a more org-level priority.
So if you have a group of product managers who are using a video messaging tool as a means to share rich context and feedback across time zones, that could be something that is mapped to a new product release that has outsized organizational impact. From there, can really tie into something where your VP of Product who has access to budget, who has this company-level priority, would be more interested to invest in a broader deployment versus just saying, "You have five users. Here's an SSO upgrade. Let's get an additional 400."
Alex Kracov: I remember there's a very funny website of the SSO Wall of Shame that the old IT guy at Lattice sent me. That was like all the companies that just make you upgrade for the SSO. It's a funny thing, and I'm glad that trend has-
Pete Prowitt: The person who told you, that person at Lattice in previous, I had seen that same website from him. It was great.
Alex Kracov: Yeah, he's the best. Hello, Frank. Shout out to Frank. One thing I struggle with is the fake champion. It's like there's this end user who promises you the world. They're like, "We'll help you get into the organization." But they don't really have a lot of sway. I'm curious. How do you deal with that dynamic? How do you approach with multi-threading and making sure you're talking to the right person at the company at the customer side of things?
Pete Prowitt: Yeah, this is a great one. This is an age-old problem. There are different sales methodologies and ways to characterize it. There's one that's stuck with me. It's this idea of champions versus coaches. Both are valuable, but one is going to get you farther across the deal. Identifying who's who early is so important.
One of the concepts that we really preach on our team is testing your champions early. It's one thing to ask the question, do you have my authority? A more artful version on that. But to actually test and see through functional validation, through technical validation, through talking, through, "Hey, what past vendors have been successful here? What were the behaviors they saw? How did you shepherd them through?" You start to get a sense of, is this somebody who can actually drive me forward, or do I have to figure out another area of the company to multithread into? Man, I cannot emphasize the importance of testing your champions early and trying to validate. Because the risk you run, particularly in a tough macro-economic environment like 2023, is you spend a couple months on a deal that you think is going to get you to your number. It's just a lot of wasted calories on something that pushes or ultimately doesn't close last because the person that you're dependent on or a group of people you're dependent on can't ultimately get you to it.
One of the things that has been emphasized in recent months is, you really want to get a sense of your prospect's business model and how they make money, profit margins. This is easier to do when you're selling to publicly-traded companies, where you can go into different reports that are filed. But if you can get a sense of it's just a business model that appears to be growing, that appears to be viable, you can have a higher level of confidence in those deals closing. Because dollars maybe aren't as hard won.
In businesses that are suffering outsize right now, you run the risk of just a new CFO or a new initiative coming in. Even if you have the right buyer, spending freeze, it's just happened overnight. Trying to go through your pipeline and fine-tooth comb and say like, this is a business that's growing. This is a business where it's not easy money versus hard money. But you're not going to be under the same level of rigor if you're in a business that's thriving versus a business that's going through a tougher patch.
Alex Kracov: You touched on the macro and how things are a little bit different now in 2023. I think it started there. You have the benefit of perspective, right? You've been doing this for a while. We're hearing the good times and then the zero-interest rate environment. I'm curious. Are there other trends you're seeing in what makes selling now different than the early days of Intercom or even before that?
Pete Prowitt: Yeah, I remember when I first joined Box, it was coming off of a really tough macro with the 2008-2009 financial slowdown and just trying to get back. One of the things that at the time felt like a real challenge when I look back, and I'm very thankful for, was business cases were hard won. Deals were hard won. ROI was a part of every conversation, hard stuff. I think that in a tough macro, the idea of ROI is always important. But it is so important to establish early to understand how does your service make or save someone money. Then being able to flesh that out early, come to mutual agreement, and then every single conversation, touchpoint and technical validation that you do, has to map back to that why and sort of the how do we make or save your money.
I talked to a CRO who had sold his company service to a FANG type company a year ago. It was a 100k deal. It required two signatures. It was a relatively fast-deal cycle. This year, to renew it at the exact same level after a relatively successful first year, it required 17 signatures. And so just little things like that. How many people are involved in the buying process, and what's the level of scrutiny over each dollar? It's a small anecdote to me, but it's just a reminder of every single thing you can do to run a tighter sales process and to harken back to a strong ROI case is the best way to safeguard yourself away from losing deals, missing targets, et cetera.
Alex Kracov: How do you think about building that ROI case? Because when I tried to do this in the past, it feels like I'm always - I don't know. I'm building some ROI calculator in an Excel Google Sheet and making up these metrics and stuff. What's always hard about it is I don't know their business that well. I don't have how much their sales reps cost. And so I don't know. What's this balance between? How do you do that? Do you just make up numbers? Do you ask them for inputs? What do you think is the best way to build that ROI case?
Pete Prowitt: It's easier to do in some spaces, in some industries than others. I think that the key - particularly when you're in a newish space, or you're taking a new approach where ROI isn't just generally accepted - is that really collaborative feedback and making sure that you get mutual agreement, mutual buy in at every step.
If you can get to the space of saying, "Hey, I'm going to save you 100 developer hours per month. From what I see, you have 20 developers on LinkedIn. I'm ballparking what their annual salaries are. Based on what you told me before, it sounds like you're spending x number of hours working on these projects. Is this accurate?" At some point, if you're taking those thoughtful approaches and you're getting really collaborative, people will share. Like, this a real problem I'm feeling, things like that. They can also say, "I don't think 100 is real. Maybe you can only save me 50." But the key is, if you're going through that ROI calculator, if you're just depending on the ROI calculator that somebody puts on a marketing website with a bunch of inputs, I think that is usually met with a level of skepticism, where if you can go through that mutual validation process, you're a little bit more likely to come up with something that is defensible.
Alex Kracov: Very interesting. I'd love to switch gears and talk a little bit about you personally and your transition into a revenue leader. Over your career - we talked about this before - you went from an IC to a manager. Then at Rewatch and now at Stytch, you're a VP. You're VP of revenue. And so I'm curious. What is that transition like? What do you think is the biggest difference between being a revenue leader, sort of at the VP level, versus being a manager on a sales team?
Pete Prowitt: I think that at each stop - I've just been really lucky to work at great companies who've been funded by great VCs. I get to work with really smart people. At each stop, the key is really trying to figure out what is your special sauce that you bring to the table. What is your superpower? And how does that tie into something that is important to the company right now?
I think with each kind of place that I've worked, I've developed a different skill set. At Box, for me, it was really learning the enterprise sales book. At Intercom, it was really trying to figure out like, hey, for an early product-led growth company, how do you build a go-to-market team? How do you build a sales team that is truly complementary and not cannibalizing self-serve, adding value, helping move up market, and driving that dollar retention? At these different places, you learn how to tap into your background and your skill set and figure out how to have the most impact.
I think that the thing that I love most - I've discovered this over the past couple of years - is when you're building zero-to-one or one-to-five teams, everything you do has outsize impact. Everything you do, from hiring a person, setting a culture, setting a performance bar, reinforcing that performance bar, it sets the table for the next 3, 6, 18 months. I think that it's a combination of the scrappiness and just figuring out how to get things done, doing things that don't scale. But also, just trying to look around the corner and think if I am setting this performance bar now and we're anchored at this level, is this going to be something that helps us 18 months from now? Is this the right kind of standard to set today? That's something I'm always thinking about. I'm always trying to figure out how can we make sure that we're setting ourselves up for the better next 12, 24 months.
Alex Kracov: It's like the first 90 days of leading a revenue team is just so important, especially when you come in from the outside. There's just a lot of trust you need to build in both directions, with the sales reps on your team and with the leadership team. And so, how do you think about building trust? Is it getting quick wins? How do you think about coming in and just making an impact right away?
Pete Prowitt: It has definitely evolved over time. I think that a failure mode that you see sometimes, and I fall into in the past, is you want to come in and just hit the ball at a park right away. Sometimes you can be more prescriptive than really trying to understand what are the problems that we're facing today, how the different teams interact. If we take as a use of systems thinking approach to this, what are some of the functions and dysfunctions that we really want to lean into over the next quarter or quarters? I also think that, depending on the stage of the company you join, you don't want to get too strategic and far away from deals and deal execution.
The worst thing that you can do particularly in a year like this is to drop the bomb execution. Every CRO I know, every VP of sales I know has been more deal-level focused this year than they have in the past 10. I think that's because there's a real opportunity cost. Pipeline is hard won today. It's sort of like trying to balance the organization's priorities and your strengths and skill sets at the time, but also just knowing what's going to be most important, trying to be that chameleon. For me, right now, I'm toggling a little bit further back into deals, making sure that of the pipeline that we have, that we're executing as best as we can. I'm constantly learning what plays work, what don't. I think that that's more of a broadly-shared trend.
Alex Kracov: Yeah, let's talk about that, your current role at Stytch. Stycth is - correct me if I'm wrong - an API for authentication and identities. You sell primarily to developers. That's a little bit different than what you've done in the past. And so I'm curious. How do you approach selling to developers? I can't imagine they enjoy talking to salespeople too much.
Pete Prowitt: I don't know. I think I'm pretty fun to talk to.
Alex Kracov: Yeah, you are.
Pete Prowitt: You are absolutely right. I think for Stytch, which is an API-first and developer-first platform for building authentication that supports not only password base but a lot of passwordless authentication flows, what we're doing is we're taking this problem that people have solved in a very straightforward way, with passwords being the backbone for authentication for the past 50 years, and really turning it on its head in some ways and figuring out how do we become the bridge to passwordless? How do you reduce friction on the internet for your users? How do we make sure that people are seeing the value of your product and getting to those aha milestone moments as fast as possible?
What we found is, over the past year, we have a really technical buyer on deals where there's not a VP of engineering or there's not a CTO. It becomes very hard for us to sort of sequester the engineering resources we need to test to validate, and to get real feedback on what migration would look like, and how the solution design authentication. And so, for me, the challenge is that this is the most technical product I've sold, and it's also a really technical buyer.
One of the things that I've learned over the past year is figuring out an outsize role of solutions engineering having really technical counterparts, and then figuring out the interplay between more process-focused account executives and sales professionals, and then where to plug in those solutions engineers. As somebody who's worked in partner selling with solution engineers at many different steps along the way, I have never appreciated that team more than today. Because I think we got to this point where the AE and the sales professional becomes responsible for the what. Why are we doing this? What are we looking to do? Then the solutions engineer becomes the how. It just created this really powerful dynamic that's led us to bigger deals, better deals, and to more traction as we start to find our groove on that front.
Alex Kracov: How does that collaboration work? Because you have the AE. You have the solutions engineer, and then you obviously have the customer who's a developer. Are you sort of all collaborating in a sales proof of concept document? Do you have a shared Slack channel? Because there must be just a lot of next steps you're sharing or to-dos and things. There's just a lot of alignment that needs to happen. And so I'm curious what that looks like practically.
Pete Prowitt: Totally. Well, I think most AES have heard some version of you become the quarterback of your deals type speech. But in a deal like this where it's technical stakeholders, it's technical leaders, then it's really important to meet your individual contributor developers on the right level and then to figure out how to solve problems for both of them over the course of a deal. There's a lot of coordination that happens internally. And so that'll be an AE working not only with their solutions engineer, but potentially interacting with folks on our product team, our engineering team to talk through roadmap, talk through how to proof of concept different things, trying to figure out, hey, if we advise in this direction, is that going to create complexity later on?
And so it's a lot of Slack channels. We'll have internal Slack channels for customers. We'll have external Slack channels with customers. It's figuring out like, what are the best ways for us to to drive that internal collaboration? So that at each call, we're coming in not only with a well-prepared presentation and well-prepared demo, but also really thoughtful and bespoke solutions designed for customers that are going to help them solve today problems and future proof them. When you're selling a core infrastructure, the future-proof piece is so important. Because nobody wants to rip out authentication more than once every 5, 10 years. So proving out that you're going to be the best long-term partner is so key.
Alex Kracov: Yeah, it puts more emphasis just on those technical proof of concepts. The good thing about Stytch is, once it's in there, they're probably very unlikely to turn. It's a very sticky product, which is awesome.
Pete Prowitt: We love to do our job. But yeah, that's the fun part of it.
Alex Kracov: I'd love to end on a fun note. I think before business, you are a basketball player, right? You played for Stanford's basketball team. And yeah, I don't know. I'm curious if there's any lessons you learned from sports that you apply to sales. Anything about that experience make you a better leader?
Pete Prowitt: Yeah, I feel like I can fall into the stereotypical former athlete goes into sales model. But for me, I really don't feel comfortable unless I'm in that team environment - in a team environment where you're pushing yourself really hard, but you're also pushing each other. I remember having very candid conversations with my coaches, with my point guards. Sometimes my point guards didn't give me the ball on the right block in the exact place I liked. I would have very candid conversations with them. But there's something that's so comforting and functional around a team that is holding each other accountable, a team where you really feel like you win or lose together, and a structure where you put a lot of accountability and emphasis on your own performance. For me, that was such a natural transition into sales.
After basketball, I had a chance to play briefly overseas. I had a couple of different jobs. I was a speechwriter at an international organization, which is kind of fun, as an investment banker very briefly in Boston during one of the snowpocalypse. But I didn't really find that environment that was a proxy for what team sports was, until I got into sales. For the past 12, 13 years, it's been a really happy place.
Alex Kracov: I think that the funnest part about sales is that team rah rah sort of environment. I started my career at Yelp. That was definitely what it felt like. I feel like with the pandemic and remote work, we've maybe lost a little bit about that. But maybe the pendulum is swinging back, so we'll see. We'll see what happens. Thank you so much, Pete. This was a wonderful conversation. If people want to follow up with you, ask questions, promote yourself. Where the best place? LinkedIn, Twitter?
Pete Prowitt: LinkedIn is a great place. If you want to drop me a note, I'm just pete@stytch.com. Thanks so much for the conversation. It's really fun.
Alex Kracov: Thanks so much, Pete.
