“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

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We recently chatted with Jeanne DeWitt Grosser, Chief Business Officer at payments giant Stripe. Jeanne helped build much of Stripe Sales from the ground up, driving go-to-market strategy and building many of the specialized functions required to support complex customers. After seven years running go-to-market, she’s now leading Stripe’s Global Partnerships (think Visa, Apple, Klarna, banks) and Corporate Strategy organizations. Prior to Stripe, Jeanne was the Chief Revenue Officer of Dialpad. She was also a Director of Sales at Google, where she led SMB and mid-market sales for Google Workplace in North America, LatAm, and APAC. 

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You joined Stripe when the U.S. sales team had about 10 people, and pretty much built the GTM org from the ground up. How did you approach that challenge, and what were some of the biggest sticking points as you grew the team to over 400?

Jeanne: Stripe is a Product and Engineering-led company, so the first challenge was building a Sales organization that was culturally congruent with the rest of Stripe. We focused deeply on product knowledge (at one point two-thirds of the sales team had taken Stripe’s coding class!), and even did small things like use engineering terminology to describe sales activities.

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As we began to move up-market, another challenge was getting the company comfortable with outbound prospecting. There were big concerns about contacting developers or sending emails with content that wouldn’t be perfectly on brand. So, we developed a documented philosophy and set of operating principles just for outbound. We centralized content creation, built out a massive database with sophisticated propensity models, and ran each campaign as a “sprint” with documented hypotheses and A/B tests. (If only AI had been a thing in 2017…)

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When we got into enterprise, we wanted to ensure that we didn’t create “roadmap schizophrenia” by selling functionality that our engineers didn’t want to build, or that sales wouldn’t be able to sell to the next enterprise prospect. So we created a “lighthouse list” of key logos and aligned at the top on pursuing them. We convinced a small tiger team of tenured engineers to be our “Lighthouse Engineering” team to attend sales calls with us and help determine what to build to accelerate enterprise readiness, and oftentimes build that functionality themselves.

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You’ve been with Stripe for nearly 9 years now, tell us about your move from Sales to Partnerships? What were your key motivations, and how did you know it was the right moment to make the move? 

Jeanne: Billy Alvarado was Stripe’s first business hire and Chief Business Officer for ten years. When he left Stripe, I felt like there might be an opportunity to work in a critical area for Stripe, bring a slightly different lens given my commercial experience, and ensure Stripe didn’t miss a beat since someone who gets payments, understands Stripe’s business model, and is both product and business savvy can be a bit of a unicorn.

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When I thought about the job, I felt like my experience in sales would transfer well to the relationship management and business development parts of working with partners. I’ve always been a product-oriented sales leader, so I also thought it would be really interesting to actually work in our Product organization and learn more about how products actually get built. Finally, the role was global and covered business development, but also partner engineering and operations, as well as risk (and ultimately Corporate Strategy a bit later), so I felt like I would broaden my functional experience and solidify my global leadership.

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The Chief Business Officer title isn’t all that common in the C-Suite, what does the role at Stripe entail, which functions report up into it, and what are some of the key differentiators from other C-Suite roles? 

Jeanne: Partnerships at Stripe is pretty different from many other tech companies because Stripe’s products, for the most part, don’t exist without an underlying partner. We partner with Visa, Mastercard, Apple, Klarna and many others to take payments. We work with 20+ banks around the world to move money. We partner with other technology providers to augment our software offerings like Stripe Tax. Additionally, the commercial agreements that we have in place with these partners also meaningfully impact Stripe’s financial performance – we’re often exchanging tens if not hundreds of millions of dollars of value with any given partner. Further, any fintech has to deal with financial and regulatory risk. So, my job touches on most functions at Stripe, and partnerships brings them together to provide the backbone for our business.

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One of the things that I think is somewhat unique about the role is how evenly it’s split across Horizon 1, 2, and 3 work. In any given week, I might be involved in handling an incident with a partner experiencing downtime, then negotiating with a partner to unlock a product we’ll launch 18 months later, and then brainstorming how the ecosystem dynamics between banks, networks, and regulators might change the landscape for Stripe in five years.

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What’s the best advice you’ve received - or given - about how to manage people?  

Jeanne: I’m sure a lot of folks have been told about the “platinum rule” – effectively, you need to manage others the way they need to be managed, not the way that you personally like to be managed. This advice has always really stuck with me, particularly given that I became a people manager at a very young age, and so I really had to work to earn the respect of my direct reports.

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When I take on a new direct report, in my first one-on-one, I always ask how they prefer to interact with their manager, as well as what was true about the best manager relationship they’ve had. That helps me figure out the “how” for supporting and motivating that individual.

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I generally spend a lot of time aligning on the “what” with my directs – what’s the outcome we’re trying to achieve on what timeline, what are the metrics or other indicators that will demonstrate we’re tracking towards that outcome and have ultimately reached that. Once we’re aligned on that, I can approach the “how” very differently with each person reporting to me – some want detailed reviews of drafts, some want to do high level brainstorming, some just want to come to me when they need unblocking. Every approach can work if you have an aligned North Star and understanding of how to collaborate.

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What was one of your first jobs and what’s one big lesson you learned? ‍

Jeanne: My first job out of college was answering Gmail support tickets. If you contacted Google in 2004 wondering why we didn’t have a contacts list, if you could get an invite, or whether we were reading your email, I probably answered that email. In 2005, we launched POP-access so you could get your email into Outlook. The feature was pretty technical and buggy. No one on the support team wanted to work on it. So I took it on and painstakingly answered all of the tickets (I even snuck into the office – no real VPN in that era – to answer tickets until 2am on a Saturday to clear a backlog). As a result, there was a point where I probably knew more about the product and our users than anyone else on Gmail.

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I think folks grossly underestimate the value of knowing your products and your customers better than anyone else around you. Throughout my career, I’ve always sought to recreate my “Gmail POP” knowledge base, and as a result, I very frequently find myself in influential roles in meetings that my job description wouldn’t necessarily have suggested I should be a part of.

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How have you made a mark in your industry? What’s something you’ve done that’s perhaps counterintuitive in your field - broken any rules with interesting results? 

Jeanne: I’m generally a big believer in knowing best practices, but applying first principles. There’s no point in reinventing the wheel if it’s working well, but similarly, you shouldn’t blindly follow something that worked in a potentially different context.

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In the early days of Stripe, we were very non-traditional about two traditional components of a sales organization: sales compensation and sales engineering roles. On the former, most advice would have suggested that we should have individual sales targets with something like a 60/40 base/bonus comp plan. We had team targets for quite some time with a low leverage plan. Sales philosophy would say that this approach shouldn’t create a high performing org, focused on driving quarterly revenue. Our experience was that everyone was highly focused on putting up the biggest number, while ALSO being exceedingly collaborative, willing to do non-sales builder work, and think about how today’s actions impacted our long-term outcomes.

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Similarly, I was shocked when I started at a company that sells an API and we had no technical sales resources. But I quickly learned that Stripe’s world-class docs made it so that our prospects were effectively their own SEs. On top of that, with Stripe’s engineering-centric culture, having AEs who took a coding class and deeply learned about how our API worked meant that Sales was deeply ingrained in the fabric of Stripe, rather than a function off to the side that felt different.

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What’s a piece of advice you would give to yourself 10 years ago, if you had the opportunity?

Jeanne: I would have told myself to work on my external community sooner. I tend to be pretty obsessed with whatever I’m working on, which can create a bit of tunnel vision (all Stripe, all the time). A  couple years into Stripe, I started having more opportunities to engage with the VC community, other startups, and other revenue operators. It's been an incredibly enriching experience because it’s enabled me not only to share my knowledge and experience where it’s helpful, but also to stay on my toes by learning what other leaders are doing, as well as having to apply my insights in a different context.