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

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

As he makes the transition from operator to investor, Meka Asonye looks back on his career as a sales leader at Stripe and Mixpanel to offer tactical takeaways and go-to-market lessons — crowdsourcing additional advice from the top revenue leaders in his network.

When Meka Asonye 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 (acquired by Slack), Coda, Stytch, and Snackpass.

And as we announced last week, 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 over here. 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 Angel Track, 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.

  • Andrew Berger - VP of Global Sales at Front, formerly at Square
  • Charley Ma - GM of Fintech at Alloy, first business/growth hire at Ramp and Plaid
  • Claire Hughes Johnson - COO at Stripe, former VP at Google
  • Jeanne DeWitt Grosser - Head of Americas Revenue & Growth at Stripe, formerly at Google
  • Kenny Mendes - Head of Finance, People & Operations at Coda, formerly at Box
  • Kyle Parrish - Head of Sales at Figma, started as third sales hire at Dropbox
  • Liat Bycel - VP of Sales at Airtable, formerly at Twitter
  • Matt Hudson - Head of Growth & GTM at Coda, formerly at Google
  • Richard Alfonsi - former Head of Global Revenue & Growth at Stripe, VP of Global Online Sales at Twitter
  • Sam Taylor - VP of Sales & Success at Loom, previously first sales leader at Quip and first enterprise sales rep at Dropbox
  • Shruti Challa - leads Revenue at Sonder

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 they 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.


“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 product/market fit 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 — Stripe Atlas and Stripe Press 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.


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 Coda’s Matt Hudson.

“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.”

First principles: pricing

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 Stripe Atlas summaries 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,” says Hudson. “I’ve written about 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.”

His colleague Kenny Mendes (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.

First principles: comp

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.

First Round Partner Meka Asonye
Meka Asonye, Partner at First Round and former sales leader at Stripe & Mixpanel.

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,” says Jeanne DeWitt Grosser, 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.”

Richard Alfonsi (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,” he says.

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.”

Sonder’s Shruti Challa 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.

Trying it out:

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.”


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.

Founders who hang on to sales too long:

“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 give away that Lego. “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.

Figma’s Kyle Parrish 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.”

Charley Ma 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 Alloy and first growth hire at Plaid.

Founders who give sales away too early:

“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 Claire Hughes Johnson. (In our view, her Review article on 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.”

Andrew Berger, VP of Global Sales at Front adds his perspective: “I spent months at the hip of Mathilde Colin 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 serious 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. “When you outsource too quickly, you don't know who 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.”

First Round Partner Meka Asonye
First Round Partner Meka Asonye

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

  • How detailed are you able to get on your ICP? “Segmentation is not enough,” says Asonye. “A vague ICP is ‘Series B technology companies.’ An extremely detailed ICP has the company stage, company industry, buyer persona, current solution, and potentially, trigger events too. ‘Companies who are experiencing X, who look like Y, who have previously tried these three solutions and need the product to do A, B, and C ’ is a good starting point.”
  • Can you tell the potential hire what the trigger events are for your customers to consider a new solution?
  • What features are vitamins, painkillers, and/or table stakes? How does this vary by company size and persona?
  • It comes down to having a truly introspective look and thinking about, do you have any sort of repeatability in the business? How many customers are at the top of the funnel each month? How long should it take them to convert? What are the steps required to go from awareness to paying customer?

Loom’s VP of Sales & Success Sam Taylor adds another: “Before you make your first sales hire, figure out and take inventory of what you’re articulating around the value and vision of the solution. You need to capture the way in which folks are finding success on your platform and put that into a digestible format that can be delivered by a salesperson credibly,” he says.

Coda’s Kenny Mendes offers up a specific heuristic that could come in handy as you scale beyond that initial first sales hire. “We've tried really hard to find ways to measure whether our product was ‘good enough’ or ‘ready’ before pushing for growth by adding more sales people,” he says. “Internally, it's a tagline called OCUC — are we 'Of course use Coda’ for that use case? Holding this line and investing first in eng and product fixes, then product specialists, and so on, has led us to building sales and success motions that should scale much better long term.”

Founders who make the wrong kind of hire:

There’s a slew of different kinds of mistakes founders can make in this bucket — here we run through a few potential potholes, offering up some tips for how to swerve to avoid.

  • Needing growth or marketing first. “Many founders start hiring for sales when what they really need is to hire their first marketer or growth person,” says Asonye. “This is especially true for the founder trying to do bottoms-up. Sales is great, especially if you're banking on an outbound motion. But for many mid-market and SMB-driven companies, the first key is marketing. Top of funnel needs to be there before you go out and hire a bunch of sellers,” he says. Figma’s Kyle Parrish agrees: “Sales isn’t marketing and sales. It's just sales. Early founders forget to pair their early sales hire with someone good at awareness and conversion. Be explicit on distributing revenue growth across multiple people,” he says.
  • Hiring the big name too early. “Be very honest about what the company needs in the next 12-18 months. If early-stage startups hire a Head of Sales, but the reality is that they need a super driven, self motivated sales person who is excellent at closing deals but can also help build the GTM strategy, the profiles and skill sets are different,” says Airtable’s VP of Sales Liat Bycel. “You need to have conviction on the size of org before you decide what leader you need. Don’t hire the big name too early — get people who want to roll their sleeves up. Think two years ahead for all hires,” says Figma’s Kyle Parrish. Stripe’s Jeanne DeWitt Grosser agrees. “There’s a tendency to hire folks who look great on paper, but who are way too senior for the current stage of the company and don't know how to get their hands dirty anymore. By hiring two years ahead of where you are currently, they can grow into the leader, but they'll still be close enough in experience to what you need today,” she says. “As a rule of thumb, I don't think most leaders can handle scaling back more than one order of magnitude in org size — for example if you currently have a 10 person sales team, look for someone who's led a 100 person sales team, but not 1000.”
  • Overlooking the skills needed outside of sales. Table stakes is their ability to deal with ambiguity, says Coda’s Kenny Mendes. “There are phenomenal reps who can be excellent hire #5 and up, but you really need to hone in on a special breed for that first phase,” he says. Airtable’s Liat Bycel adds a nuance here: “It’s critical to not only hire folks with a flexible mentality, but those who are highly coachable and are highly skilled in both receiving and implementing feedback,” she says. Here’s how ex-Stripe and ex- Twitter leader Richard Alfonsi thinks about it: “The criteria for GTM hiring considers broad buckets like domain/industry experience, functional experience, and overall horsepower. Of course you'd love for a candidate to check all the boxes, but there will almost always need to be trade-offs and prioritization,” he says. “I'd also look for early folks who are particularly strong around product — they will need to be able to get deep into the product to bring its value to clients and to channel super-valuable product feedback back to the company.  They also need to be able to earn the trust and respect of the engineering team.”

Alfonsi also encourages founders to take a step back and shift their mentality on sales hiring. “I've had lots of discussions with early-stage technical founders who are — often uncomfortably — thinking about making their first business, GTM, or sales hires, at a stage when nearly all the company is composed of engineers. They're often nervous that this step may introduce a foreign element that will dramatically change the culture and make-up of the company,” he says.

His advice? Don’t think about sales or GTM as a radically different organization. “It is not some coin-operated function to be bolted onto the side of the company, or some group of mercenary foreigners with radically different culture, DNA, or motivations,” says Alfonsi.

“The best sales folks ‘fill in the gaps’ in the org to make things happen — they collaborate effectively across all functions and bring them together. What they bring to the table is the mindset, energy, and specific mandate to close business — along with the skills and the functional expertise to do that.”

If done right, this team will be a mission-critical partner in the dual challenges any tech company faces: building stuff and selling stuff.


“Slack, Asana and other ‘bottoms up’ companies have popularized the self-serve ethos of ‘If you build it they will come’ — and that is simply not true for most companies,” says Front’s Andrew Berger. Coda’s Kenny Mendes adds on: “A belief I’ve changed my mind about is that your product has to be ‘easy to use’ to activate users and grow quickly. There have been many counterexamples to this lately,” he says. (The growth stories of companies like Snowflake come to mind here.)

These observations might come as a surprise, given how en vogue product-led growth and bottoms up strategies seem to be these days. But that’s precisely the point. “The last wave of successful companies like Calendly, Atlassian and Slack have proven it out. It’s great, especially when you’re targeting SMBs. If you're trying to sell an SMB and you don't have a product-led approach, you probably don't have a sustainable business model,” says Asonye.

“That said, there are still other ways to win in this world. There are companies with a squarely enterprise product, and out of the gate they need to be able to serve enterprises. And I think it's probably one you see less, but it is still a viable path depending on your product and how users will adopt it. Not everyone can start with self-service or free trials, and then monetize from there.”

Everyone wants to be product-led and self-serve, but there are some products that don’t lend themselves to growing in that way — in part because there are some organizations that don't adopt products in that way.

Alloy’s Charley Ma shares his change of heart here. “I used to believe that enterprise deals should be avoided early on. I do still believe that chasing whales has a high probability of killing early-stage companies — from dragging on product requests to string-along contracting — but not every company needs to start with small deals and move upwards into larger, enterprise deals,” he says. “It's a very common growth path in Silicon Valley, as selling to tech-forward startups is often a much faster way to get numbers on the board. However, if the ICP and problem-set you're solving for is truly enterprise, then sometimes it makes sense to tackle that GTM early on and set that as your big hairy goal.”

Figma’s Kyle Parrish serves up a simple yet important reminder:

Good sales leaders focus on building a machine as well as the craft of sales. Create a list of what you need to sell your product.

This again may require challenging conventional sales playbooks. “It is never, ever too early to start outbound prospecting,” says Stripe’s Jeanne DeWitt Grosser. “It always amazes me how long it takes to build this muscle with your sales organization, particularly after folks get comfortable with being ‘fed’ by inbound demand,” she says. “If you're getting a ton of inbound, that's actually a sign that you should be scaling far more rapidly — hire enough salespeople so that inbound is still a scarcity and people are forced to prospect from the get-go. Doing so will help you avoid hitting a plateau — eventually your inbound demand won't be able to meet your year-on-year growth needs. Build ahead of that point.”


As GTM leaders settle into their roles and founders continue to sharpen their sales skills, this group serves up two broader lessons that make for apt parting thoughts: leave room for bad weather and get ready to climb the jungle gym.

“Earlier in my career I was somewhat maniacal about having my process and team ‘dialed in.’ Every question had an answer. Every process had a sequence. Inbox zero or bust,” says Matt Hudson. “But while we were in the earlier stages of Coda, I read Creativity Inc and there was a great metaphor in there about managing people with an understanding of the weather. You’re going to have rainy days, cold days, sunny days, and so on. You can’t fight it. Human beings (and organizations by extension) are similar. Sometimes leaving a little space to let things simmer ー being okay with the disorderlyー enables you to focus on bigger issues and allow for some creativity.”

Stripe’s Jeanne DeWitt Grosser shares this career lesson on growing in different directions: “I constantly have to relearn that the most robust career path is a jungle gym. I always push myself into trying to find the most linear and vertical career path, only to realize that I've skipped steps in my own learning curve, or I have legos that I need to give away,” she says.

“For example, for the past three years, I've effectively been the ‘CRO of the Americas’ for Stripe — I ran sales development, sales, technical sales, implementation, and customer success across all segments. It was an excellent experience to build many of those functions from the ground up. However, as we enter a stage of hypergrowth, I was the right person to take a lot of those functions from 0 to 1, but I need to hand them off to a leader with deeper functional expertise to get them from 1 to 10 (and likely 10 to 100 as well). It's not easy to give up things you've built, but our organization will be better off. I similarly think that I'll be more likely to be able to run them again in the future, by handing over the reins today.”

Photography by Bonnie Rae Mills.