Successfully Scaling Developer Products with Customer-Led Sales

Michael Grinich (00:02):

Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving up market to serving enterprise customers. I'm your host, Michael Grinich. I'm the founder of WorkOS, which is a platform that helps developers quickly shift common enterprise features like single sign-on. On this podcast, you'll hear directly from founders, product leaders, and early stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics, and real world advice for ways to make your app enterprise ready and take your business to the next level. Today I'm joined by Paul Williamson, former head of revenue at Plaid. Paul's worked at companies at all stages of growth from pre-revenue startups all the way through Fortune 100. At Plaid, he played a pivotal role in driving revenue growth from single digit millions to hundreds of millions. And before Plaid, Paul led go-to-market teams at both Visa and Salesforce. I'm excited to dive into how Plaid crossed the Enterprise Chasm with Paul. Welcome to the podcast.

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Paul Williamson (01:05):

Thanks for having me, Michael. It's great to be here.

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Michael Grinich (01:07):

So to get started, take us back a little bit. Let's talk about your experience at Plaid. When you joined the company back in 2017, what were things like then? What was the customer base like and maybe kind of more specifically on the go-to-market side, what was the state of the world there when you came in?

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Paul Williamson (01:23):

When I first joined back in January of 2017, it was a very different company to what Plaid is today. But we had about 100 clients when I first joined the company. I had a couple of people in the sales team, and Plaid overall was about 50 people total in terms of company size. And as you mentioned, we were single digit millions in terms of revenue at that point of the company's lifecycle. And what was really interesting for us when I first joined is that we were very much doing a developer focus and a developer oriented, often people are now referring to that as PLG or product-led growth was the way that we were focused as a company.

The business was focused on a very specific buyer or user of our product and technology. So you would consider them a developer who wanted access to financial data, was really the person that we were very myopically focused on in the early days of Plaid. So they were building an app that wanted to be powered by financial data. And again, we were lucky because our first customers were the likes of Venmo, Robinhood, Acorns, Chime, Coinbase, et cetera. Amazing first customers to be joining a company at, but very much sort of like early developer, building the new wave and phase of what was the start of FinTech.

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Michael Grinich (02:53):

Those are some amazing first customers, any company would kill to get those. How did that happen? How did the company get those users initially? Was it right place, right time, the approach of the product? What would you chalk that success up to in that early cohort that really propelled the initial growth?

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Paul Williamson (03:10):

When you actually considered the landscape of the competitive environment that Plaid was in, there was a number of competitors that were already in market, actually in some cases, a little bit before Plaid and in other cases well before Plaid. But I think while we were late to the party and all that kind of stuff, one of the things that we, as I said, we were very, very focused, if not myopically focused around, was essentially the developer. And were we building not only a great product for the developer but all of the other things that would make a developer successful. And so things that we considered as real game changers for us in terms of going out and not only engaging but acquiring those customers well, I was like, "Do we have absolutely the best level of support? Do we have great documentation?"

Particularly like technical documentation for us was just such a hallmark of what we did at Plaid. And they were the bookmarks for us internally at the company because we made it easy for people to go from downloading the API key to getting integrated and getting value from the product and getting it as quickly as they possibly could. And to be perfectly honest, I think one of the real big things that stood out for us and something that we heard back from a lot of those early customers of Plaid was, you just made it easy for us to become successful. You made it easy for us to use your product, you made it easy for us to start to see value in what we could do. And I think one of the big leading differentiators for us was particularly around the technical documentation side.

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Michael Grinich (04:50):

Can you walk me through how those signups or those users turned into real businesses? The ones you're mentioning are really, I would imagine a company like Robinhood being built on top of Plaid, a pretty huge type of customer. How did they evolve? Because the docs get you some part of the way it's people to see it and integrate it. But for a customer like that, it's probably not the only thing.

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Paul Williamson (05:10):

It's not. It was a very, very important start. I think what we also were able to recognize very, very early on is Plaid was such an important part of the enablement of their customer, which is where things made a really big difference for us, which is we recognized that we needed to have a great and high quality technical product and technical documentation that goes with it. But what we also recognized was that for a Robinhood customer and consumer to go and literally make their first trade, we also had to make sure that we built a really amazing consumer experience that was part of Plaid's onboarding process to really make sure that when the ultimate customer of the Robinhood application was using Robinhood for the very first time, was it easy? And was it simple? And so technical documentation was one part.

But the other big component that we focused a lot on, and this was something that really stood out for me about Plaid early on, is that the two co-founders, Zach and William, cared massively about product design. And particularly product design in the eyes of the consumer using the Plaid application in Robinhood and the easier that we could make it for a consumer to go through that onboarding process, the more value we created for Robinhood, Coinbase, Acorns, Chime because it just meant that they would do so much hard work to acquire the interest in someone to use their application. But that would all fall apart if the consumer couldn't find it or couldn't navigate through the onboarding flow, couldn't find their bank account, the OTP or the MFA process didn't work for the consumer. All of those things were points of breakage and so we knew that not only did we need a great technical product, but we also needed a great consumer facing capability that ultimately the customer's customer would love. And that was super important.

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Michael Grinich (07:20):

So back then Zach and William are chugging along, acquiring these customers, growing and then they call you to join. And they say, "Hey Paul, we really need help with X." What was the call for you to join the company? What did you really see as your job coming into transform? Can you talk about the shift that happened, I assume, over the first year coming into the company and what different strategy they were looking to drive with you on board?

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Paul Williamson (07:45):

I think one of the interesting things with Zach and William is number one, they really did have a product that was there that solved a very important problem, which I think every co-founder and founder goes through that. First idea, first ideation and getting those first customers. And their big focus was that we want to bring someone on that can actually help us go and transition from very much a founder-led sales process to building an established go-to-market capability inside the business.

And so that was really the phase and stage that I joined was we're wanting to transition from being founder-led to actually building a much more formal go-to-market organization. And particularly the first four years that I was with Plaid, I was obsessively focused on really helping drive and build the acquisition engine for Plaid. So really making sure, and this was a company ethos of ours then and it's still a company ethos of Plaid’s now, is how to make sure that anyone who is developing and building an application that needs to be powered by financial data is doing that with Plaid. But they wanted to make sure that we could go build a really, really scalable and robust go-to-market engine for the business.

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Michael Grinich (09:07):

Tell me about the initial team you started building around that. Because in that early days you're probably not looking to bring in the seasoned folks you worked with at Salesforce or Visa and with an established engine. There's a lot of learning and kind of zero to one building that you're doing there. How did you think about who to hire and how to build that initial crew that was going to lay the groundwork for that new go-to-market motion you just described?

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Paul Williamson (09:30):

I was really lucky because I had two great founding team members that I inherited when I joined Plaid. So huge props to Kate and Charlie for them being the ones that I got to work with initially. That was an amazing start and nucleus to the team. But we were still very, very early on as we were transitioning from being founder-led and moving into building a proper go-to-market team, and really what we were looking for is people that could do a lot of the components of the go-to-market process. We wanted people to be able to sell and do some customer management and customer success. We wanted them to write the first call deck and we wanted them to do writing some content and building case studies and things like that.

So we weren't going to go pluck, like you suggested, the more traditional salespeople out of large established companies because in a lot of cases, those roles in those large companies have become very narrowly defined. Like I'm an AE in this market segment and this is the kind of customers in this market vertical that I want. And that level of focus and specificity in the role, while that's good for large established companies, was not great for Plaid. So instead, really the hiring philosophy and the people that we were looking for is that we were looking for this, I would call them the decathlete. They were a high functioning athlete, but they could play 10 sports or they could do the 10 activities across go-to-market that were really, really important for us.

And so we were really trying to find people that could be really great at a very, very strong cross-section of a lot of the different skills that are important to go-to-market. Again, we weren't looking for that really niche specialist. We were looking for the people that could do 10 things and do that to the 80 to 90% mark and do that really, really well, particularly because what was our go-to-market to begin with was going to evolve pretty quickly. So we needed people who had that in-built playbook of a few different things and some level of adaptability that we could grow and then morph from as well.

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Michael Grinich (11:39):

Where did you find you found those people? Maybe someone's listening to this podcast and thinking, ah, I need three of them tomorrow. Where's the decathlete store? How did you evaluate those kind of skills? Because I feel like if you're looking for that domain experience that you're saying is not a good fit, that's a pretty obvious profile to go find someone seasoned with a resume XYZ. But this more general purpose decathlete, I'm curious, were they coming from non-traditional backgrounds? And how did you assess their ability to play those 10 sports?

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Paul Williamson (12:05):

I think, and people talk about this a lot, which is about the diversity of hiring that you can bring into a company, and we were really focused on skill diversity, that was really important. And I think the way that you go drive and find skill and knowledge and experience diversity is you look in a lot of different places. We actually very actively avoided large enterprise companies and things like that for that very fact. Again, I'm not casting dispersion on the importance of people who work at those companies, but I'm just saying for early stage companies, they just were not a great fit. And so instead, that we would actually look at other small companies, other early innovators, other early phase, end stage startups, and the things that we were really, really interested in was I wanted to see an entrepreneurial bend to these folk. Have they been in an environment similar to Plaid? And have they had to be able to do a multitude of different jobs and different roles in that?

Or more importantly, were they willing and interested to do those things? So we would spend time really getting to know the potential candidates. And I think for me, I was asking more alternative questions than the typical sales leader in those kind of conversations. A lot of people would be like, "Hey, tell me about your quota and your quota achievement and what kind of territory you work today and where are you at kind of quarter today?" Sure, I can ask those questions and that was really interesting. But I'd ask questions like, "What was the most recent book that you read? And what was something that you did to challenge yourself? What was the last thing that you learned? What was the last thing that you taught someone else?" And it was those kind of elements, those kind of things that were really different and a little bit unique and we just found, especially early on, some amazing talent internally in the business. The first SDR, the inbound lead qualification person that we hired was a guy who went to Brown University but he, literally over the course of his last summer before graduating, was part of Hillary's campaign. And he was literally knocking door to door with a list of people to go for the Democratic National Convention to literally go and get their support for Hillary. So this guy literally had never met these people before, literally just took a list and was willing to put himself out there, go and knock on doors. And he could talk about all these super interesting conversations that he had with all of these interesting people. And I was like, man, the level of inquisitiveness and interest and also the guy's willingness to put himself out there, I was like, I want to hire this guy. We have to hire people like this. And it was a lot of folk like that, wouldn't be considered by most traditional companies, but for us, we were like, "Holy smokes, that  is the kind of person, that is the kind of character, that is the kind of spirit, that is the kind of entrepreneurial approach that we not only want, but we need at Plaid."

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Michael Grinich (15:16):

I feel like working on a political campaign might be the only thing just as hard as selling to developers. Notoriously difficult to do both things. Let's talk about that maybe, kind of the developer sales motion. You start pulling in these decathletes, you start thinking about evolving the go-to-market motion to include actually having people do sales and work with customers. I've seen a lot of examples of companies where they start making this transition and suddenly everyone has to contact sales. Suddenly the signup button is gone or the pricing page says contact us, there's no more of public pricing. And the pendulum swings super hard the other way. They squeeze as hard as they can to get as much revenue as they can to give up the self-serve side. How did you navigate this at Plaid? How did you figure out maybe what the rules of engagement were of self-serve versus this team working with customers? And really, how did you think about navigating that to figure that out in those early days?

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Paul Williamson (16:09):

I think one of the important things is that that was a founding principle for Plaid, was that we were always self-serve, customer signup flow first company. And ultimately, that has never changed. In fact, over the six and a bit years that I was there, we continued to evolve and offer more and more of our products over time via self-serve versus narrowing it and narrowing it. Even as our sales teams and revenue teams got larger and larger over time, a lot of companies start to de-scope what can kind of happen from a self-serve perspective. We actually found the opposite, which was opening up that scope is actually more valuable for us, and we learned that more and more and more over time. But we also recognize that there was value in both a customer-led motion versus a sales led or a business led motion.

And one of the early things that we did really, was start to define and qualify early about who was coming into pipeline for us. And then really being thoughtful about navigating where they wanted to go or where they should go for us. And a lot of that actually, in some cases, was essentially the audience, like the person who was on the other side of the conversation with us. And particularly for the developer who was like the early engineer, integrating Plaid into said financial application, what we knew and what we continued to double down upon was like, well let's not be in this selling mode with these guys. And I think, Michael, you can probably speak to this experience yourself. You're probably being sold to all day and every day by anyone who wants WorkOS to be a customer of theirs. The vast majority of the time, you don't want to be sold to. And in your case, you want to go and learn and experience that product. And so what we realized is that we should be doing this one thing.

There's this old sales saying, which is ABC, always be closing. That's a very sales-oriented approach to things, which is give to the sales team, they should essentially be focused on getting a deal done all the time. And that is not the principle that we would ever follow with a developer-led or customer-led sales cycle. We believe in this other thing called ABH, which is always be helping. Help that person get the information that they need. And that could be through technical documentation, that could be maybe through sharing a customer case study, that could be maybe should be showing them a better way to do the integration to the API than what they'd already done themselves. The focus was help them be better with their products and services. And by helping, by nurturing in a lot of cases for those clients, we just got out of their way. (18:52) But there would be other cases where the audience was a different kind of buyer category for us. So maybe this was the head of growth, it was the chief commercial officer, the head of revenue at that prospective customer.

Well, that's where we would want to go have an engaged sales cycle or maybe the product was a little bit more technical than some of the basic solutions that we had and there needed to be an appropriate sales cycle based on the use case that they had. And that's when we knew, hey, we actually would want to pull this thing in to be actually run as a sales cycle. (19:27) And then later on, as we got bigger and we started to move up into the enterprise and things like that, we would often become a lot more prescriptive about when we would want self-serve to act versus it being led by an internal team. But again, that was something that we continued to change and evolve over time. But we did have to recognize that there were distinct differences between buyers and what they wanted from us in that sales cycle. And we needed to be the one to adapt ourselves to that. More often than not, people forced the prospective customer to adapt to them, which is never a great place to start.

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Michael Grinich (20:04):

I love that ABH, always be helping. It's a little different than the Glengarry Glen Ross sales culture. I want to ask you about sales culture. I think a lot of people that are maybe developers or startup founders or product leaders have had lousy experiences in sales. Maybe they get reached out to all the time, or it's someone blocking their ability to get something done. And there's this idea of the salesperson being the kind of like playing golf, smoking cigars, eating steak dinners, driving Porsches, the kind of million dollar smile.

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Paul Williamson (20:32):

All of the cliches. Yeah, yeah, yeah.

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Michael Grinich (20:35):

All the cliches. The kid that was the bully to you if you're a geeky programmer when you were in high school or something. I've noticed the cultures of these two worlds just kind of having stereotypes on both sides like that. You joined Plaid and built not just the sales function, but also the sales culture of that organization, bringing it closer to engineering and product. I was wondering if you could just talk about how you thought about that cultural crafting process and where you were aiming to land. And when you left Plaid, where did you leave the sales culture at that point? What had you built it into?

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Paul Williamson (21:08):

What was interesting is that we spent some time as a company, defining the values that we had as a company, which I think was a really important thing. Jean-Denis, who was the head of engineering and is now currently the CTO of Plaid, also then at a function level went off and defined some values for the engineering team, which I thought was interesting. I'd seen companies build their value systems, but I'd never seen subteams build their value systems before. And it was pretty inspiring to think about the sales and revenue org and its value system and how it sat with inside the broader value system of Plaid. And so we actually went through an exercise about, I think 18 months or so into my time there, to really go off and define those values for us inside the business.

And we had four official values and then a fifth extra value, we'll call it the bonus value, that we built out. But the values were number one, was be a vanguard and so be a vanguard. I won't bore you with the really weird military history of this, look it up later. But there was a vanguard World War II. But the vanguard was also this whole concept of be a thought leader and work with your customer to share value and share knowledge, ABH, always be helping. The second one for us was this concept of leave no stone unturned, which was like to be unbelievably thorough in all the things that we would actually do and really ask all the questions, the hard ones, the easy ones. But ask all the questions, even ask the questions that even our competitors wouldn't ask to go through the process.

The third one was grow together. You can learn anything from everyone inside your team. You just have to be willing to be open to learning from other people. And then the fourth one was win as a team, which is obviously really focused on doing things together as opposed to doing things in isolation. The fifth bonus value was this thing called shoot your shot, which was like if you're going to go have a crack at something, really go have a crack, don't hold back. But we really built and instilled a value system inside the team, and we really used that also as a framework or a rubric for the kind of people that we hired, the kind of people and characteristics that we were looking for.

But it was a very impactful thing because I think both Plaid as a company and then us as a rev org inside that business, we were intentional about creating and defining the culture that we wanted to create. But then the last piece of that was that, and this is I think where building a culture is one of the most important things, is that because I was the leader of it, people would assume that I am the person who drives the values inside the business, which is actually, I think a bit of a mistake. I really saw myself as a steward of the values, but then every other person was a contributor to the fulfillment of those values inside the organization. And that distribution of value definition, creation, and ownership was super important for us.

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Michael Grinich (24:18):

Spoken like a true leader. Paul, thanks so much for joining me on this podcast to talk a bit about your experience at Plaid.

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Paul Williamson (24:23):

Thanks for having me, Michael. I really appreciate it.

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Michael Grinich (24:31):

You just listened to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving upmarket to serving enterprise customers. Want to learn more about becoming enterprise ready? The WorkOS blog is full of tons of articles and guides outlining best practices for adding features like single sign-on, SCIM provisioning and more to your app. Also, make sure to subscribe to this podcast so you're first to hear about new episodes with more founders and product leads of fast-growing startups. I'm Michael Grinich, founder of WorkOS. Thanks so much for listening and see you next time.

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