Between Sales and Product: Building Out Self-Serve and Customer Experience at Notion & Dropbox

 was graduating from the University of Southern California in the midst of the recession — not the optimal time to be job hunting. She took a chance and sent a cold email to Marc Benioff (a fellow Trojan). Within 10 minutes, the founder responded and introduced a recruiter to Taylor, who ended up landing a role as a corporate sales rep.

That email kicked off what would prove to be an impressive career in tech. Taylor left Salesforce to join Dropbox in 2012, starting in support and moving into channel and sales development. She spent the better part of the decade figuring out the company’s famous self-serve funnel and refining the product feedback loop, ultimately leading their SMB revenue and scaled sales operation. Fast forward to August 2020, when Taylor joined 

 as their new Head of Customer Experience, a role that combines products, sales and support to run what she calls the “front door experience” for customers (more on that later).

Here on The Review, we’re struck by how Taylor has strung together a fascinating set of experiences, from the classic top-down sales motion she saw at Salesforce, to the bottoms-up adoption and 

 that propelled Dropbox and Notion. She’s built a career that, as she puts it, has been focused on finding the balance between sales and product — a skill that’s in high demand these days. 

As founders are increasingly leaning into 

 and self-serve strategies, there are plenty of potholes to derail their progress. For both sales-driven companies that are intrigued by self-serve and 

bottoms-up businesses wrestling with when to layer on sales

, Taylor makes for the perfect guide. In this exclusive interview, she unpacks common traps and tensions, comparing and contrasting her experiences at Dropbox and Notion to offer up sound advice on finding the middle ground between sales and self-serve. She also delves into strategies for thinking through pricing and packaging, approaching product prioritization, and building a better customer experience.

From how Notion’s incredibly tight product feedback loop works, to the pricing experiments Dropbox learned most from in the early days, Taylor shares a treasure trove of helpful anecdotes and actionable tactics that will have founders and go-to-market leaders taking notes (in Notion we hope).

SHIFTING FROM SALES-LED TO PRODUCT-LED: FINDING THE MIDDLE GROUND BETWEEN ENTERPRISE AND SELF-SERVE

Taylor was in for a world of change when she made the leap from Salesforce to Dropbox. “When you’re building a company, you're trying to figure out who is that target market? Where is the company the best fit? At Salesforce, that was very clear when I came in. I learned a lot about targeting specific segments and what that flow should be like, especially when the average deal size is extremely high,” she says. 

“In transitioning to Dropbox where it was more product-led, that model flips on its head. You have to look for opportunities for self-serve to lead and sales to follow. The question is more about 

 and how product can drive the sales funnel. Ultimately, I've ended up nestling myself in between product and sales. At both Dropbox and now Notion, our perspective was that 

we don't want to leave customers behind. 

Finding that middle ground was super pivotal.”

Instead of forcing a sale, focus on getting to the right place — and testing to make sure you’ve arrived.

But the process of unearthing that middle ground took time. “The team that I ran at Dropbox was called inbound sales. At first, it was part of the sales org, but we eventually realized that wasn't a good place for it. When people came to the website, they had interests across different categories. Maybe that was buying, maybe it was support needs, or wanting to know about partnerships — my team was actually more of a routing function,” says Taylor. 

So we moved into the marketing org, took quotas away and started to make it more of a value-driven effort to answer questions and get people to the place they need to be

. And that often may have been over to the sales org, but it could have pushed them into the self-serve flow or over to support. Once we discovered that interacting with customers should be more of a value-driven conversation, that was when things just started to click.” 

The team was starting to get customers to the right place instead of trying to force a sale.

 that things were clicking. “We actually started testing this at Dropbox. Once we got a little bit more intelligent with how this team was operating in between go-to-market and product, we ran experiments where we held out a set of control customers and compared them with a variant group to test if these conversations were driving value,” Taylor says. “

 and less on revenue, and then see what happened compared to the control. And we saw a considerable lift in revenue

. Reps were motivated off of having value conversations and answering the quick slam dunk questions that customers had.” 

There was value in it for sales folks as well. “Customers end up in self-serve and they may have questions and aren’t quite at the sales line. Now sales was saying, ‘Thanks for getting this customer the answer, now they're in a trial,’ or ‘Now they're ready for a much larger discussion because they understand a basic need,’” says Taylor.

It's easy to put up barriers on the site or make it difficult for customers to get in touch. We did the opposite at Dropbox, believing that value would drive revenue and LTV. And we actually tested that to be true.

Build a land-and-expand flywheel and grow alongside your customers.

The handoff between self-serve and sales became a well-practiced alley-oop. “At Dropbox, we found that the goal of self-serve was landing teams and getting them to love the product. And then sales was about taking those teams and helping them understand the value of the product up market — as opposed to the traditional model where you've got sales cold calling and trying to source these wall-to-wall deals,” says Taylor.  

“Completely honestly, looking back at Dropbox, that cold sale just did not work. And we tried it quite a few times in enterprise. Instead, have upmarket sellers focus on what they do best, which is selling wall-to-wall deployments and getting people using and loving the product at larger companies. And then self-serve is focused on creating product-qualified leads for that type of motion.”

If you let the product lead and sales follow, this natural flywheel starts spinning and it starts to click for customers.

This thinking translates well to Taylor’s role at Notion today. “We want to lead with getting people into the product, understanding it, and then building that adoption and groundswell for sales to go and sell into,” she says. “We’ve seen that many of these enterprises started as smaller deployments and as they've grown, these needs for our more advanced features kick in. And that's when we start to have that sales conversation. It usually happens with growth and maturity. And the relationship we’ve built along the way is what enables us to have that conversation.”

 as an example, says Taylor. “They started as part of our startup program, with about 20 seats. And now they’re using and loving Notion as they've grown and scaled considerably. That’s an ideal use case of a company that's growing significantly and finding leverage with Notion — brought in by a self-serve program and as they grow, our sales team is there to help them find additional value,” she says.

But of course, it’s not always so seamless. Tensions bubble up to the surface when the respective swim lanes of sales and self-serve are less than clear. Here, Taylor highlights potential pitfalls:

Getting caught up in a competitive streak

. “It's really hard for an enterprise team paired with a self-serve motion, because your product is always, in theory, cannibalizing itself. When you can sign up very easily, that's a really hard model to pursue because sales is ultimately fighting the product itself and product adoption.” Instead of trying to validate itself against self-serve, the sales team should adopt a different mindset, says Taylor. “Instead of constant competition between enterprise and product, what we should be doing is making it really clear for customers that if you're of this certain size and these are your needs, then this is the product for you. Instead of competition, it should be about creating a healthier funnel.” There’s potential bristling on the self-serve side as well, but a mission-focused mindset also comes in handy. At Dropbox, Taylor’s team was charged with figuring out where customers were falling out of the funnel and serving up conversation at those points to both help the customer and learn about the friction points in order to drive that feedback back into the product. Counterintuitively, 

Taylor’s goal for her “self-serve assist” team

 was to make self-serve so much better that she’d ultimately have less revenue and a smaller team over time.

“What really worked at Dropbox is that self-serve became a land motion for companies of all sizes, and then sales was focused upmarket, for companies of 250 or more.” But company size isn’t always a clean dividing line, however, Taylor cautions. “It's easy to say a company size is a great way to divide up customers, but that doesn't always work. The buying process for a five- to 10-person team at Nike might actually mirror a buying process for a SMB,” says Taylor. “So what you really want to think about is some kind of line between team size and company size — and making it as easy as possible for someone to get into the product.”

“As you layer on self-serve, if that side starts to take off, you might back off of the enterprise feature development. It’s tempting to shift away and start to build more on self-serve,” says Taylor. “But at Notion, we're taking an opposite approach, which is: Self-service taking off. That's great. Even though it’s going well, if enterprise is where we want to be, then we need to continue building out functionality that supports it. And ultimately it will go down market and benefit all users,” she says. “It's that dedication factor — when one starts to win, do you shift resources? Trade-offs in those moments are difficult and it's the dedication piece that often can shift in a world where you don't have unlimited resources and you have to make a decision.”

Self-serve isn’t about competing with sales, it’s about creating a healthier funnel. There are tradeoffs and tensions along the way, but you need to stay the course.

PRICING, PACKAGING AND ONBOARDING: LESSONS FROM EXPERIMENTS AND UNITING USE CASES

Pairing self-serve with enterprise sales can cause a wrinkle over on the pricing page, however. That’s because there’s a menu of options to choose from — charging for incremental features, per seat, based on usage — and competing incentives. “As we are looking at pricing and packaging at Notion and which type of model we want to pursue, the licensed model always makes sense for us in an enterprise setting, just because as you think about distribution for users who are coming on and off, it's the easiest way to manage,” says Taylor. 

“But there's a component for self-serve and SMBs where usage is actually a major driver, so thinking about paywalls around usage or with the free product tend to be the easiest way to drive value quickly.”

To illustrate the impact this has on customers, Taylor serves up an example from her Dropbox days. “Dropbox views their website as a product. The goal is conversion — we wanted people to start as many trials as possible, and the pricing page was one of the biggest conversion opportunities,” she says. “My team saw that there was heavy drop-off for users after around 30 seconds on the page. And so as an experiment, we started to put chat just below the 30-second mark, with the goal of catching users right before they dropped off to figure out why they were stuck and ultimately serve that feedback back to the product team.”

Here’s what they discovered: “The users coming to the site had no idea which plan they were on. So when they're looking at which plan to pick, they don't even know where they're starting from. I mean think of Netflix — what plan am I on? I don't know what it's actually called,” she says. “And so it was a very simple product fix — if the user is logged in, illuminate which plan they currently have to help give them the idea of where to go.”

For Taylor, this was both a key learning and a proof point in the value of self-serve. “Afterwards, we could quickly spin down that chat on the pricing page. A bunch of users were able to convert because of this change and that flywheel that my team continually built with product,” says Taylor.

In these pricing and packaging moments where all of us are so focused internally on what we're trying to differentiate and build for each tier, we lose sight of the fact that the page can drive a lot of confusion and that our users don't even know what tier they're actually in.

Focus on activation, but don’t lose sight of the user’s context

“At Dropbox, we used true-up models, where you pay for a minimal amount of seats, and then look back at the end of the quarter to see how many people are actually using the product. Those models tend to work in the early days, but become a bit difficult to continue when counting revenue. But it starts to give you an early indication of how adoption is going,” says Taylor. 

“With a company like Notion where there's a lot of viral adoption upfront that doesn't tend to be necessarily the biggest issue — users are already using and loving the product. It’s more about bringing multiple self-serve teams together, all under one umbrella,” she says. “At Notion, our sales team is looking to bring in all of that usage and have that conversation around why it’s important for Notion to be that central hub for a company, versus a collaboration tool on a single team. The value is really when you've got different departments in different groups using Notion together.”

But illustrating that is important — which is why onboarding and activation is so critical. “In trials, we're trying to prompt users to take different product actions and create a more active workspace. The key here is the 

One key learning from Dropbox was to keep metrics as simple as possible here

. We used to do health scoring across 15 different dimensions, and it was really hard to move the needle on any health score when you have so many different factors.”

In addition to keeping things simple, Taylor learned the importance of not losing sight of your user’s context. “We did a lot of retention experimentation with self-serve at Dropbox. We were trying to rewind back to that moment where you had to be engaged — as in, if you weren't engaged past X time, you just weren't going to renew,” she says. “We did a bunch of campaigns to reverse through the life cycle and ultimately found out that if you weren't active in the onboarding period, it was unlikely you would reactivate.”

But this is where your product builder bias can creep. “

We had specific situations at Dropbox where users were not technically active by our definition, but when we engaged with them, we actually found that it was an indispensable tool and they couldn't live without it. 

And it was because they were storing all their information in there, they knew it was safe and they trusted the product, even though they didn't access it regularly,” says Taylor. 

“It was a good reminder to continue to test your user base, talk to people and engage with a variety of different segments and really understand what they value. So often you sit in your own environment and that's really not what your users are experiencing,” she says. “We’re sitting here in San Francisco on our Macbook laptops, but that’s not how most of our users experience the product. I try to remind myself of this every day at Notion. Most of our users aren’t in the U.S. and so it's important for us to put ourselves in the shoes of our users and continue to check what's important to them on a regular basis.”

Unite use cases through product “aha” moments and the power of community

Of course, this journey of activating small teams, getting adopted by larger teams and then expanding into company-wide deployment brings the challenges of juggling multiple personas and use cases to the forefront. “We used the 

 at Dropbox. It's important to understand the different jobs that someone is paying you to perform for them. And with different departments, each one is going to have a different need,” says Taylor. 

“In terms of product strategy, it's a real challenge to decide whether to go deep in one specific area or go wide over specific use cases, and in a world where you obviously don't have unlimited resources, you have to pick one specific direction and pull out the common themes. 

For self-serve, it’s about trying to create the ability for users to identify or find common ground with personas

. That was ultimately what we tried to do with Dropbox,” she says. “At Notion, we're trying to make it really easy to unlock people's use case early on through templates.”

Taylor points to a fresh example. “Right now we're building out a 

. We've had it moving now for about a year and a half, and we're trying to make it easier for startups to unlock the value of Notion in their context. So for example, you might have pitch decks that you're trying to put together, or you're getting an early product roadmap in place. When you start your workspace, how could those things just exist there for you so you can dive in and start using them in real time?” she says. 

“For the sales team, for example, that might mean having a 

 that was pre-built. And so through templates, we're trying to get into these use cases so that it doesn't feel as nebulous or as much of a white space. 

In the sales process, you obviously try to identify use cases upfront. But in self-serve you've got to use the product to actually make your way there. It’s about unlocking that quick “aha moment,” but then bringing you along to uncover new ways to use the product.

In addition to templates, Notion is making use of its 

 to help users find value in the product. “One of the biggest things I've seen at Notion that's different is 

. We have an amazing network of folks who preach how to use Notion and do all of this viral marketing for us,” says Taylor. “And these people are running their own business as a consultant, teaching how Notion works on YouTube and holding meetups and seminars in their own communities. They're actually creating templates and selling them themselves. And out of that we spun up this 

Unlocking this professional-level service community outside of Notion has enabled the team to tackle product onboarding at scale, says Taylor. “It’s really powerful. 

I’m actually even using some of our amazing ambassadors and consultants to help with training and onboarding for new Notion employees

 — there are some very passionate and expert-level folks in our community who we can leverage more, even internally.”

Our community keeps us tapped into the real work and tangible value people are finding in the product — as opposed to just what’s happening in our heads. 

PRODUCT PRIORITIZATION: BALANCING NEEDS AND BUILDING A BETTER FEEDBACK LOOP

Layering sales on a bottoms-up self-serve motion is a highwire product balancing act — developing the features that enable product-led growth and deliver on what customers want, while investing resources into the enterprise features that will enable more upmarket wall-to-wall opportunities. Here, Taylor gives us a window into how Notion and Dropbox approach this conundrum.

Commit to a course, instead of thrashing back and forth.

If Taylor has one piece of advice, it’s to commit.

In the early days, Dropbox didn’t have the conviction to commit to enterprise she says, and in her view, that ended up being a mistake. “When I started at Dropbox, we basically released a team product that had centralized billing and we only did it because some users said, ‘Hey, we need to be able to pay for all these accounts on one credit card.’ And then slowly but surely we added some engineers and resources to it,” she says. “But it was a bit thrashy because we pivoted every couple of years. We would go hard on enterprise and then back off and move to building photos. Then we’d shift toward enterprise and then back off again and move toward consumer docs.” Without decisiveness on the company strategy front, bringing on an enterprise sales team but failing to point the product in that direction can cause sales to flounder.

At Notion, however, it’s a different story. “Through the interview process and since I’ve joined it’s been very clear: Notion is going to be an enterprise company. We want to build for larger companies. And so there's a balance of building features that our users need and rely on all the way to where we want to be in the future,” she says.

In a world where there's limited resources and issues you can’t resolve in six months or a year, you have to commit to a direction for the long haul.

Customer feedback is critical to help drive that product direction. The centerpiece of Notion’s efforts here? Their elaborate feedback tagging system. “Every conversation we have with a customer or prospect — unstructured emails, chats and call scripts — is manually tagged across sales and my team with our system of 700 tags.” While that might seem overwhelming, Taylor says even that’s a whittled-down list. “The real art of it is that these tags are pretty specific. So they might be specific to not just databases generally, but database properties or relational database issues,” she says.

“What’s more is that those tags actually port into our product roadmap in Notion, informing both our overall product strategy as well as the building process. As engineers are working on specific features, they're seeing real-life tallies of relevant tags on things that they're currently building for.”

Making sure that the product feedback loop is continually moving is one of the most valuable things that we've done since the early days. 

But how do they take all that bottoms-up feedback and square it with the top-down product vision? “It's basically one giant prioritization exercise. The product roadmap is driven off of our user feedback in tags, mixed with the strategy of where we actually want to go, plus this art component of 

“For example, this year we sat down and looked at the most frequently requested features, taking all the tags and looking at what was most important to users. And since we’re trying to build a product that's focused on teams and moving into the enterprise, we’re also considering the features that can help build on that use case. And then it's sitting down and looking at what's realistic to build, planning in half years.”

CUSTOMER EXPERIENCE: GETTING USERS TO OPEN THE FRONT DOOR

Soliciting and meticulously categorizing all of this product feedback connects back to the mission of Taylor’s customer experience team. Every company wants to be 

, but she’s found a way to truly operationalize the concept of caring about the customer. “In my role, I’m thinking about how we build out the ‘front door experience’ at Notion,” she says.

Here’s what she means: “My team spans across product, sales and support, and we’re trying to drive value for Notion users across all of the experiences they have with us. 

If you believe that putting customers first and having conversations with them ultimately drives LTV and increases the actual dollar value of that customer, then interacting with them should be a no-brainer

,” says Taylor. “We view the customer interaction as not a cost center, but as a requirement, as an area of investment, because that feedback enables us to continue to drive that product intuition internally.” 

The concept I like to talk to the team about is customers coming into our living room, sitting down and having a conversation with us — how do we make it feel that easy to talk with us? How do we make users feel at home when they open that front door and engage with us?

What does that look like in practice? “That means putting in more ways to get in touch and hear more from people, not less. How do we actually just help customers when they need us, making it very easy to contact us, either in the product or on the website? It means not just sending a simple link to a help center page to close out the conversation,” says Taylor. 

Much of this, of course, runs counter to traditional customer service thinking around reducing average handle time. “The customer service goal is not to get them to stop talking to us — it's actually to pivot the conversation around and learn more,” she says.

Instead of trying to avoid customer conversations, how do you make it easier for them to get in touch and find the information that they need? How can you try 

To find more signal in these conversations and surface deeper motivations behind feature requests, Taylor relies on these questions:

•Tell me why that feature is important to you.

•Tell me more about your business and what you're hoping to accomplish

•Tell me more about your workflow that would cause you to ask this question.

Instead of influencing their thinking or referencing existing features, these questions help hone in on their deeper needs — the things they’re really trying to do. “The goal is to help identify more of where Notion could drive impact currently or how we could change the product to drive more impact in the future. It's this feedback loop and it helps users understand that what they're talking to us about is actually critical to the company,” she says. “Again, it goes back to this concept of living room hospitality — we want them to feel like they're part of the process with us. They should leave every conversation feeling like they made an impact.”

This ethos can be traced back to Notion’s early days DNA. “We were very, very focused on engaging with every single user on Twitter. We would get back to every single person, and we still do that today. Customer obsession has to come from the top down, and Ivan has always been very focused on reading direct feedback every day from our users to drive what's in his head and where he thinks Notion is going.”

Yes, helping one user will help them individually find value and understand the product. But they're part of larger communities — and if you believe that writing the best story with that user then allows them to go tell someone else about the product, that’s how you unlock that viral growth.

This article is a lightly-edited summary of Kate Taylor's appearance on our new podcast, "In Depth." If you haven't listened to our show yet, 

Car driving over a bridge and body of water

Self-Serve Lessons From Dropbox & Notion

Kate Taylor spent 8 years at Dropbox leading their SMB revenue and scaled sales operation) and is now the Head of Customer Experience at Notion. Here, she shares actionable tactics on getting product-led growth, self-serve and customer service right — from how to build a tighter product feedback loop, to lessons from pricing and packaging experiments.

Notion's Head of Customer Experience shares tactical lessons on closing the gap between product and sales.

Between Sales and Product: Building Out Self-Serve at Notion & Dropbox

This GTM-Leader-Turned-Investor Crowdsources Early Lessons From Stripe, Figma & More

 first started his career, he was laser focused on talent development, on spotting potential key players and giving them a shot at the big leagues — and we mean that literally. He wasn’t leading startup recruiting, but rather managing Minor League operations for the Cleveland Indians and advising their GM on roster and payroll allocation through advanced statistical analysis.

It may not seem like the typical springboard into the world of startups, but Asonye has since strung together a set of experiences that any company builder would envy. He’s been both the startup’s early sales hire, and the VP leading a 100-person global revenue team, crafting repeatable playbooks at every stage of the company building spectrum. 

Asonye spent four years cutting his teeth at Stripe as it scaled from 250 to 2000 people and matured its sales org. He then stepped into the VP of Sales and Services role at Mixpanel, owning the customer lifecycle from first website visit to renewal. He’s also been an angel investor, seasoned advisor and first call for dozens of early-stage consumer and SaaS startups, such as Rimeto (

, Asonye’s taking on a new role: that of a full-time investor, joining us as a Partner here at First Round. We’re brimming with excitement to add him to the team — you can read more about that 

. But from our perch here at The Review, we spotted the chance to tell a different story. 

If you’re a long-time Review reader, you’ll know that we’ve long believed the best company building advice comes from fellow practitioners, and Asonye’s startup experiences are still incredibly fresh. (As he puts it, he owned a quarterly number just one quarter ago.) Whether you’re trying to figure out founder-led sales, building out the customer success function, or working through thorny cross-functional issues on an executive team, he’s been in your shoes very recently — which makes him a uniquely helpful leader to learn from.

So as he hit the ground running in his first few weeks at First Round, we pulled Asonye aside to unearth some of those lessons, mining for those go-to-market insights that others could lean on. He came back with an intriguing proposal. While he was of course game to share his own takeaways from across his nearly 15-year-career, Asonye wanted to reach out to others across his deep network of sales, growth and customer success leaders to crowdsource the very best advice.

“My mom always said, ‘You are an average of the five people you spend the most time with,’ and that’s really been a driving principle across my career. The common factor between all my different roles is that I’ve focused on being a sponge and learning as much as I can from others,” says Asonye. “

A person’s career isn’t just about what you learned — it’s about all the people who helped you soak up those lessons and come to those realizations along the way

Below you’ll find the standout collection of experts Asonye assembled for this crowd-sourced guide. Some of those lessons came courtesy of folks Asonye met as a member of 

, First Round’s curriculum-based community for emerging angel investors. Others he was in the trenches with at Stripe. Many are fellow GTM leaders he’s regularly traded notes with. 

 - VP of Global Sales at Front, formerly at Square

 - GM of Fintech at Alloy, first business/growth hire at Ramp and Plaid

 - Head of Americas Revenue & Growth at Stripe, formerly at Google

 - Head of Finance, People & Operations at Coda, formerly at Box

 - Head of Sales at Figma, started as third sales hire at Dropbox

 - VP of Sales at Airtable, formerly at Twitter

 - Head of Growth & GTM at Coda, formerly at Google

 - former Head of Global Revenue & Growth at Stripe, VP of Global Online Sales at Twitter

 - VP of Sales & Success at Loom, previously first sales leader at Quip and first enterprise sales rep at Dropbox

Drawing from his experiences at Stripe, Mixpanel and angel investing, Asonye blends his advice for founders and GTM leaders with the words of wisdom these experts offered up. What lies ahead is an inside look at the advice that’s often only shared through backchannels or 1:1 mentoring — including the mistakes founders and early GTM leaders often make, the conventional startup sales wisdom they’ve found not to be true, the beliefs they’ve changed their minds on over the years, and the things they wished 

 had paid more attention to sooner in their own careers.

Whether you’re on the founder side of the equation, or you’re the leader tasked with revving up the growth engine, there’s plenty of wisdom in here for both groups. From how to rethink common playbooks and what you should look for in your first sales hire, to why you shouldn’t just default to self-serve strategies, Asonye and this group take us through what founders and startup revenue leaders need to know to win in today’s environment.

LESSON #1: IF IT’S HARD TO COMPETE IN THE EARLY DAYS, GET CREATIVE FOR THE CUSTOMER

“For my first role at Stripe, I was one of the first account executives when we were trying to go up market and started selling it to the enterprise,” says Asonye. “We were about 250 people, and had pretty good 

 with early-stage companies. And the bet was, can we scale this up market with a direct salesforce?” 

That may seem like an obvious question now. “Everyone looks at Stripe’s story today and it seems so up-and-to-the-right easy. But we got so many nos in the early days. So many ‘We’ve never heard of you’ or ‘How can we trust you with our payments? Are you going to be in business in a couple of years?’ kind of comments,” he says. “None of that was solved. We were getting our SOC certifications. We were going through pen tests and writing our first enterprise MSAs. It was definitely building the plane as it was flying.”

After a year as the tip of the spear of the effort to land large companies and unseat legacy players — a familiar setting for any early startup hire — Asonye’s next chapter at Stripe had different contours. “For the next three years, my job was to take our largely self-serve business for startups/SMBs and 10X our output. That included launching outbound sales, building a customer success function, optimizing inbound lead scoring and routing, developing distribution and ecosystem partnerships, opening new offices and scaling our coverage.”

But Asonye’s main mandate was perhaps a little bit less typical. “The key piece was meeting our customers where they were. 

In order to truly serve a customer, you need to understand two things: What are their goals and what is standing in their way? 

In Stripe’s case, many had heard of us because they were YC founders, or fresh out of an accelerator. So while my team and I were talking to them about payments, often the conversation would broaden to company building,” says Asonye. 

“For any ambitious founder, we wanted to make sure they felt like Stripe was a partner, so we spent time workshopping anything with them. How could a founder get value from talking to someone on our team, whether or not they ended up using Stripe's product?” he says. “We tried all kinds of experiments here, such as going to a city during their startup week and hosting a panel on what SaaS founders need to know to expand globally. Credibility with founders was core to our brand and DNA and it was cross-functional work — 

 were a part of this effort. But my team was focused on putting a human element on that work, and getting more one-to-one or one-to-a-hundred interactions with our target customers — founders.”

I’m a big believer in teaching with every touch. We wanted people to feel like Stripe was a fountain of wealth for building and scaling an effective business — regardless of whether or not they became a customer.

In Asonye’s experience, founders often forget about one of their most strategic advantages: their depth of knowledge in a field gained from hundreds of customer interactions. “

You can really differentiate yourself from the competition by serving as a strategic advisor to your customers

. Don’t think narrowly about just selling your product. Consider selling the customer a solution to their problems — agnostic of how you get them there. It’ll pay off in the long run,” he says.

LESSON #2: APPLY FIRST PRINCIPLES TO RE-THINK GTM SOLUTIONS. DO WHAT’S RIGHT FOR YOU, NOT WHAT’S FAMILIAR.

The idea of switching up traditional sales playbooks was a recurring theme in the lessons these leaders shared with Asonye. “Too many founders and early growth and revenue leaders often miss the chance to approach GTM from first principles — or at least strike a better balance between using common GTM techniques and patterns to build a motion and team, versus innovating on parts that are going to be fundamental to their business,” says 

“In many instances, there tends to be a bias in the tech community to overweight the advice and approaches from leaders of companies who have been successful, versus those that weren’t,” he says. “Sometimes, a really smart operator or idea might just be applied to a product that didn’t work out. Perhaps as an analogy, you don’t judge someone’s swing based on their pitch selection.”

To see this first principles GTM thinking in action, consider how Coda approached pricing. “There are tons of guides and materials out there around how to price SaaS products, like the 

 ー and some seemingly straightforward options. But 

determining the right model for your business can be as fundamental as designing the core features of the product

 how our ‘Maker-first’ perspective inspired our monetization model — essentially, at Coda we based many of our pricing choices based on patterns observed in how our product spread within organizations, rather than the typical approach of charging one price for all users or establishing a bunch of paywalls when someone is sharing.”

 (Head of Finance, People & Operations at Coda) agrees. “Our value of 'right over familiar' led down some very unique paths that still seem crazy to the outside world but feel so obvious to us. Now, we're seeing other companies switch their pricing model to be more like ours,” he says.

For Asonye, this example reminded him of how they similarly applied this kind thinking at Stripe, but in the area of comp. “There’s a traditional playbook in terms of how you compensate sales folks and motivate them. At Stripe, we did things differently. We had team quotas for individual lanes and that's not something that you typically see. And for our first year, we had around a 10-person sales team with no variable compensation,” he says.

His former colleagues from Stripe share a window to the thinking that went into this approach and the benefits they’ve seen: “Most startups seem to jump pretty quickly into traditional sales compensation models — 50/50 base and bonus and a more cash-oriented, rather than equity-oriented comp plan. 

There seems to still be a very strongly held belief that the only way to get salespeople to perform is to put them on a leveraged, pay-for-performance plan

, Head of Americas Revenue & Growth at Stripe. “I think this approach is detrimental because it doesn't get you or your early salespeople the opportunity to experiment and learn. It also means that, in order to be fair, you're going to need to invest in aspects of SalesOps a little earlier than you may otherwise want to.”

Giving your early salespeople equity-heavy compensation will keep them there for the long haul. These lower leveraged plans will give them the space to experiment and learn. 

This move also helps keep your sales and engineering cultures aligned, she says. “It takes a village to win most early enterprise deals, and no engineer loves hearing that a sales rep made $1M on a deal they likely did a lot of work on as well. Eventually, you’ll want to evolve your sales compensation to more traditional models as you really scale, but I’d encourage founders and early GTM leaders to be more creative at the outset.”

 (former Head of Global Revenue & Growth at Stripe) echoed this message around evolution.

Sales compensation plans aren’t nearly as important as you think they are in the early days — don’t obsess over them, but fully expect they will need to evolve

The first step is getting your top-line metrics right. This differs by business — ARR Bookings is most common, but that doesn’t work for some consumption driven businesses like Twilio and Stripe, where customer usage data (such as processing volume over the course of a year) is more apt.

“Even if you can’t explicitly pay people on these metrics right away — perhaps due to immature systems — the right folks will be motivated,” says Alfonsi. “If an early candidate is all about cash, they're probably not the right early-stage fit. As you put more sophisticated comp plans in place, make sure the incentives are driving the metrics, outcomes and actions you really want.”

Locking down the metrics for keeping score for the business is way more important than figuring out the details of the early comp plans.

That’s something Asonye took to heart from his time at Stripe. Nowadays, when he’s coaching more product-driven or technical founders thinking through sales comp or hiring for the first time, he steers them to focus on behaviors. “You get the behavior that your comp plan designs for. 

In the early days, I prefer to keep comp plans simple with two metrics, max

,” he says. “I also love plans that have a component focused on the entire customer lifecycle. For example, comping teams on bookings and retention can be a powerful way to ensure teams pursue the right users who will be longtime customers.” 

 emphasizes the need for a long-term lens. “Think through the end-to-end responsibility. The customers you win can have a downward impact on other metrics. For example, customers that are a poor fit can lead to high service times. Orient your metrics to be more holistic, not just around revenue and CLTV,” she says.

Asonye points to another area where approaching things differently can be helpful. “A common pitfall is failing to figure out if you're actually ready to put somebody on a comp plan,” he says. “You need to have reasonable predictability to be able to say, ‘I think you should be able to achieve X.’ It's not a great outcome if they achieve 100X, and it's also not a great outcome if they achieve 1% of X.” 

As a way to probe that readiness, Asonye relied on this tactic: “At Stripe, we oftentimes would

 try something with no teeth for a quarter. 

We’d say something like ‘Your quota is going to be X and we expect that you can get to X through Y leads.’ It wouldn’t be a goal tied to comp just yet, but we’d track the metrics, report on it, and see what it would have paid out if it were in place. If it worked out, we’d officially roll it out the next quarter,” he says. 

“That hedges the risks. It frees up room for people to experiment and actually figure out if you're ready — it’s a dry run. Once you've done it, everyone's a lot more comfortable and it removes tons of anxiety. As a sales leader, it allows you to double check to make sure you didn’t unintentionally create perverse incentives.”

LESSON #3: BEWARE OF ABANDONING FOUNDER-LED SALES PREMATURELY — BUT BE READY TO SCALE IMMEDIATELY ONCE YOU FIND TRUE MARKET PULL.

In our experience working with early-stage founders, this is one of the perennial hot-button topics, right up there with fundraising and recruiting. How can product and technical focused founders master the art of the sale with no experience — and when should they hand off the baton to a seasoned pro? Here, Asonye and his fellow GTM leaders highlight some common failure modes, sharing their tips for getting the timing right. 

“Some founders want to be in control, or are skeptical of sales so they want to maintain a close eye on it. So they try holding on for too long. I see this time and time again — and as a result, the level of service for your customers falls,” says Asonye. “When there were one or two customers, you could do everything, but with 10 or 20 customers, your SLA slows down and you shortchange potential customers.

Coda’s Matt Hudson concurs — and points out that this tendency lingers even when the founder does 

. “In terms of something I wish I started paying attention to sooner as a GTM leader, the answer is always hiring. There were a few roles at Coda that I was a bit too slow to bring in, and the moment we did, it was really obvious that I was months, if not years, too slow to do it.” 

If you’ve got a product with clear traction and in a good market, there really aren’t meaningful speed limits.

 adds this: “Founder-led sales is great when you are out selling the dream, evangelizing, and starting a category. When you start to get less engagement per lead, conversion rates drop off, and the pipeline is healthy — maybe five to 10 new disco calls — you need to hand it off to someone who is better and has more time,” he says.

Here’s Asonye’s rule of thumb for founders: “

If you think about the first customer you sold and the customer you're selling today, are you still giving that person that same level of attention that you gave customer one or customer two?

It’s also important to consider the number of active conversations, he says. “It depends on how involved the sales cycle is, but with a multi-stakeholder enterprise sale, you probably can't sell them more than a handful of deals at a time. If you've got five legitimate companies squarely in your ICP that are deeply engaged, then you are probably the bottleneck — and it’s time to start hiring.”

 recommends that founders start hiring for a senior VP of sales earlier, as soon as they’ve nailed down your ICP and established a path toward repeatability. “It'll take much longer than you think to source, hire, and onboard — I’d plan for at least 6 months. And by casting a wider net, you'll also end up finding high potential ‘reach’ candidates that you can bring into the org in the meantime,” says the GM of Fintech at 

“The other founder archetype is the one who doesn't enjoy selling, so they look to outsource as quickly as possible,” says Asonye. “I've seen it a ton of times with early-stage companies where the founder is just like, ‘I've got too much stuff on my plate. I want somebody else to do this thing. And I'm not a seller, so let me go hire a name.’”

That, of course, presents several problems. For starters, founders fast-forward through this important period of learning at their own risk. “Founders need to sell,” says Stripe COO 

how startups can grow faster by hitting pause

 deserves a spot in every startup leader’s bookmarks folder.) “They can’t miss this period of nailing down exactly who their buyer is and who their decision-maker is — and the realization that they’re not always the same — and matching that info up with who controls the budgets internally at the prospect,” she says.

 Others agreed. “There's a ton of value that you get in learning how to sell to your early customers — don't short-circuit this process by bringing in a sales person too early,” says Alloy’s Charley Ma. “That early customer discovery and collapsing the feedback loop to product improvement is invaluable to getting product/market fit.”

 adds his perspective: “I spent months at the hip of 

 to replicate how she sold Front. Those many months of iterations of the playbook that replicated her sales approach to selling Front cemented a repeatable process for the team,” he says.

You have to transplant the founder's sales brain to the first sales leader. Oftentimes, a founder thinks hiring means they can say ‘This is how I do it, now go do it 10x!’ In reality, there is 

 work to understand, role-play, shadow, and mimic how a founder sells their product.

The early handoff also tends to throw a wrench in the path of that early hire, and their odds of success, Asonye says. “

 you need. And when that person comes in, you don't know what to tell them to do — it's a recipe for failure,” he says. “I’ve seen so many founders struggling to unpack whether they hired the wrong sales person, or hired the right person but the playbook wasn’t solid yet, or whether it’s something else entirely, like a product issue. Maybe as a founder you saw initial success but that was based off of your intimate knowledge of the space and your unique ability to sell the dream. Either way, it adds up to the new hire falling flat on their face — and months and dollars that you can’t get back.”

Here’s Asonye’s litmus test for probing if the handoff is too premature:

All of our Sales articles

Between Sales and Product: Building Out Self-Serve and Customer Experience at Notion & Dropbox

This GTM-Leader-Turned-Investor Crowdsources Early Lessons From Stripe, Figma & More

Unpacking 5 of Atlassian’s Most Unconventional Company-Building Moves

Step Up Your Sales Coaching Game — Dig Into The Numbers to Help Your Reps Level Up

Mastering the Art of the Outcome: How Guru Turned Customer Success Into a Company Cornerstone

How Backcountry’s Support Reps Go the Extra Mile — And Get Invited to Their Customers’ Weddings

Growth at All Costs is Perilous — This is How to Scale Sales Sustainably

The Top Comms Mistakes Startups Make — And How To Avoid Them

Pricing Lessons from Working with 30+ Seed and Series A B2B Startups

Start Up on the Right Foot — Build a Customer Advisory Board

This Sales Plan Moves the Needle on Every Success Metric

The Most Surefire Way I’ve Found to Win Enterprise Deals