Sales & High Growth Startup Lessons From Leading North America Revenue & Growth at Stripe – Jeanne DeWittFeatured

I’m Jeanne DeWitt, Head of North America Revenue & Growth at Stripe. I’ve been at Stripe for about 3 years. Before joining the team at Stripe, I led go-to-market strategy as the Chief Revenue Officer at Dialpad, and before that, I led sales teams at Google. I have an MBA from Stanford and studied French, Spanish, Markets & Management at Duke.Ask me anything about building a sales organization, careers in sales, working at high growth startups, Stripe, or something else!
Jeanne – Thanks so much for joining us!Elphas – Please reply in the comments with your questions for Jeanne before this Friday (May 25th). Jeanne may not have time to answer all your questions, so please upvote the ones you'd most like answers to.
Do you think a MBA is necessary for a role like the one you have?
I get this question all the time from folks on my team, and it's a great one. I definitely don't think it's required, but I've personally found it helpful for me as I've found myself in the position of having to solve increasingly ambiguous and multi-faceted strategy questions. Business school does a great job of equipping you with frameworks that help you breakdown complex issues. It also gives you broad functional exposure, so that when I'm interacting with a CFO or CEO from a sales perspective, I can more effectively put myself in their shoes and anticipate the types of topics that keep them up at night. I think all of this can also be learned on the job with a great mentor, or through taking a set of topical courses outside of the job, but for some people like myself, the immersion in business school was the way to go.
What's your take on business school for young women looking for a career like yours? Would you say it's mandatory? A nice to have? Thanks for offering your help!!
See above! :) Definitely not mandatory. The only thing I will add that I always tell people considering an MBA: if you can't articulate exactly why you think you need an MBA to achieve your next career goal, you probably shouldn't get one (yet). An MBA can be great, but it's also a _massive_ opportunity cost, so I wouldn't go into it without a compelling point of view of how it is a necessary step in getting to where you want to go next.
Thanks, Jeanne - that's very helpful and keen advice.
Being a woman in sales (especially software sales) can be difficult. What skills did you pick up along your journey that made a difference? What do you wish you knew earlier in your career? What advice would you give to young women hoping to pursue a similar career?Thanks again! - I'm Léa and I founded Mivvy to help young women gain high-value career skills.
Great question! In tech, I feel like we spend a lot of time talking about gender imbalance in engineering functions, but I personally wouldn't be surprised if it were a very similar picture for B2B sales. At Google, I was one of just four senior female leaders in an organization with over 40 people at the director level and above. It's also super common to find yourself the only woman in large rooms when you're selling.Early in my career, I think I was extremely fortunate to work in an organization (Gmail) that really valued "intellectual honesty," e.g. everyone wanted the best possible answer, no matter who it came from. As a result, I think I've always felt more confident voicing my opinions and actively taking a seat at the table. I think I was also fortunate to have naturally found "sponsors" -- people with power in the organization who very actively supported my career. I now really actively pay attention to whether or not my manager is a capable sponsor and seek that out proactively when I don't have it. I think the other thing that has always worked for me is focusing on being a broad-based problem solver. I've never let my job description define my job. (I do things that are Marketing or Pricing or Product all the time.) As a result, I'm generally viewed as someone who gets things done, and does so for the better good of the organization, rather than my own immediate returns.
With your incredible background, it's been hard for me to narrow down the questions but here it goes (note: I'm at the intersection growth and behavioral science - I'm sure you'll see that reflected in my questions haha):1. You mentioned leading sales teams at Google. What have you learned about motivations and incentives when managing and leading teams across your career? Similarities? Differences? Patterns?2. At Stripe, you lead North America's Revenue & Growth; Stripe is clearly Global. Any insights you can share about the differences in target audience, their perspectives and how that affects strategy across the different regions (within the US as well as globally)?3. Finally, what do you love most about the work that you do? Feel free to answer as broadly or as specifically as you like. Thanks again for your time.Ever so curious,Pooja
1) Figuring out sales incentives is arguably one of the hardest parts of the job. Whenever you incentivize one thing, you're inevitably disincentivizing something else. Additionally, once you have a particular incentive in place, it can reduce flexibility for experimentation since at-risk pay impacts peoples' livelihood. The people I've tended to recruit into my sales organizations really value intellectual challenge, autonomy, and the ability to contribute to the organization beyond a quarterly revenue perspective. So, we've worked hard to facilitate work outside of the core sales role and ensure that incentives are appropriately aligned to account for that work. For example, salespeople at Stripe not only have a sales bonus for quota attainment, but they also receive the company bonus, which focuses more on their contributions to projects and driving our overall strategy.2) This has been a big challenge for Stripe to tackle because payments is such a localized product. Not all markets are as credit card heavy as the US, for example. As a result, we have different levels of product-market fit in different regions, and we sell to different types of customers. A big example of target audience differences for Stripe has to do with the availability of developers in a region. The US has far more technology companies than most other companies, which means we have a stronger fit given that Stripe is an API, so you need a developer to implement it. In other regions, this has meant that we've more rapidly had to figure out our ecosystem strategy to work with development agencies that help non-technical companies integrate payments. Different regions also have different levels of comfort with buying online or over the phone, so you often need slightly different go-to-market strategies by region to provide the types of channels that customers are used to buying with.3) I love the dynamism. There is no single obvious strategy for go-to-market, and what worked this year might not work next month or year based on the broader competitive and market dynamics. You're constantly having to experiment, reinvent yourself, and diagnose the root cause of what is and isn't working so that you can reinvest in the next effective strategy.
Thank you so much for the thoughtful and detailed reply!
Jeanne – Being Head of Revenue at Stripe, is acquisition or incubation of startups part of a powerful growth strategy? If so, what philosophy do you employ when considering partnership or M&A in terms of stage, product type etc. How can companies win Stripe's attention or reach out proactively? I'm Chevonae and I work in early stage VC in NA.
My experience at Stripe on this topic has been pretty different from how I've seen most other companies handle the question of investing in other startups. Stripe's roots were obviously squarely in effectively working with startups. We wouldn't be where we are today without all the startups we worked with early on. It's also the case, that many of Stripe's larger customers today (Shopify, Instacart, DoorDash, Lyft, etc.) started on Stripe as startups. So, generally speaking, Stripe tends to over-invest in working with startups when it comes to their near-run returns because we see so much upside over the lifetime of our relationship with these companies. Within my sales organization, we always talk about taking a portfolio strategy to working with prospects -- you're going to want some larger companies that you know can bring in immediate volume, but some of the most interesting customers and partners have been ones that "popped" 12-24 months down the line, so you've got to invest your time broadly as well.As far as getting Stripe's attention, we have a Startup Partner Program to work with early stage VCs specifically, and then we very proactively reach out to startups as early as we can identify them to help out.
I've been considering a transition into a growth role. In your experience does Growth fall under Marketing, Product, or a different department? What does your day to day as a Head of Revenue and Growth look like?
Ah, the "growth" title -- simple answer, totally depends! :) At Stripe, we actually have another Growth team, which is a little more like your typical "growth" role. They sit within Product and are focused on a lot of online experimentation around driving more self-service growth. I've definitely also see the role sit within Marketing. I feel like it tends to skew Product in B2B and Marketing in B2C, but that's not always true either.The "growth" part in my title is more of a Stripe-ism -- we want Sales leaders who can not only drive near-run revenue outcomes for the company, but also very much think about long-term growth, which to my point up-thread, often means taking my "sales" hat off and thinking about Product, Marketing, etc., or making investments in things that won't pay off immediately, but will be hugely valuable in the future.
What do you think is the best use of a small team's time when trying to win their first contract with a client? I'm launching a company that is like stripe but for personal data exchange. We're early days and looking for feedback and validation. Warm intros have been working well, but we want to kick up our volume of conversations to learn from a larger variety of businesses. Any advice?Appreciate your time and support of female entrepreneurs!
Are you trying to learn or close deals? And are you trying to sell to startups / growth companies or enterprises? The answer really depends...We had this challenge a bit at Dialpad when we didn't necessarily have a ton of inbound demand to go work with. We did some pretty interesting outbound experiments, which not only helped us cast a wider net, but you could start to see patterns in the types of companies that replied at all, which gave us a bit more of a sense of where we might have a fit.If you're trying to crack enterprise, my approach was always to be upfront about the ways in which we weren't enterprise-ready so I didn't invest a ton of time in a deal that would never close. I'd tell them all the reasons why our product would never make it through their SecOps, Legal, etc. teams. If they still thought they wanted to buy, then great. If they admitted we weren't going to make it through the process, then I could pivot into more of an R&D conversation to learn more about what would be compelling, and see if there might be meaningful ways to pilot.
We're in learning mode, and as you put it, looking for patterns where we might have a fit, but getting those initial meetings has been tricky. We don't have a cookie-cutter product for a start up to buy yet and are holding off building out anything too complex until we can validate the need. In your experience, is it better to come into the conversation with a specific offer for the start up to say yes/no and then use that as learning, or can more general conversations about their needs and goals and possible alignment be effective in building a longer term relationship? It seems the best opportunity for us will be with startups who don't have the budgets to do big market research projects and focus groups. If you have the time to share the outbound experiments you tried at Dialpad, I'd love to learn more.
Question 3: What are your strategies for running a successful customer meeting? (I just got off a call with a customer and am definitely feeling like there's room for improvement!)
Entire books have been written about that, but I'll give you something simple that I bet will make your next conversation better and is actually memorable. It's 3-1-2.How do people normally conduct meetings:1. Establish agenda2. Deliver content inline with agenda3. Close with next stepsWhen you prep for your next call, 3-1-2. Start by figuring out the next step you're hoping to produce coming out of that meeting. Then, come up with and agenda that you think will help deliver that result. Finally, create the supporting content.I often open meetings by saying something like, "Based on our prior conversation / your lead submission / etc., I thought it would make sense for us to cover A, B, C today. If all goes well with those topics, my sense is that a good next step is likely to be X. Does that align with your expectations?" Either they'll agree and then you can validate that the agenda will actually result in that outcome, or they'll disagree and then you can immediately ask what would be a good next step and adjust from there.
Curious to know what has been your biggest professional asset when working with high growth startups.?
I'm a naturally super direct person (sometimes maybe a little too much so...). I think startups tend to value getting candid answers that they feel they can trust. I know I'm cheating by giving a second, but I'd also say that I've always been a product-oriented sales leader. I tend to get really deep into the product and technology that I'm selling. Startups similarly tend to value expertise and having someone who can help them end-to-end.
Hi Jeanne! So excited to read your responses to the questions below!Do you have a preferred sales organization tool or process? I'm part of a small team, and keeping organized and efficient on following up with sales conversations is something we want to improve on.
I've always just used Salesforce with tasks and a good dashboard. Can't say I think that's by any means the most innovative or best way of doing things, but it works, and you don't invest in things that might not scale as you grow. (That said, SFDC is excruciating to get off the ground, or at least it was the last time I had to do it myself...)
Question 2: What are your strategies for converting a conversation with a potential client into a sale?
Hi Jeanne! I'm the founder/CEO of Hederis, an early stage startup in a niche industry (book publishing). We're on the cusp of really focusing on revenue and client acquisition, so I have a few related questions for you, which I'll post in separate replies so that you can pick which ones to answer. Here's the first:1. If you were building a sales team from scratch for a small startup, what are the main things you would look for/prioritize?
Jeanne, thank you for taking out time to answer here!I'm a co-founder of pulp and currently handling all part of sales and we are at early stage. In fact, We are growing fast.So as you mentioned here you were lead for sales team at google. My questions are : 1. What qualities should a candidate have for sales role? 2. Are there any specific interview questions you think one should ask ? 3. Should we have work interview as well? 4. Do you think a candidate should have particular graduation degree ? Please share your thoughts or any other relevant valuable insights you think we should know for hiring !
I just started in a national expansion role recently - any tips for identifying opportunities for growth? It's tempting to go for the shiny obvious projects that the C suite hands down but I'm interested in learning to be a bit more creative in identifying my own opportunities. Thanks, Jeanne!
Are you planning Paypal integration any time soon? To elaborate, the reason for this question is that some of my friends complained that carts get abandoned when there is no paypal payment option. The reason is supposedly because their customers view paypal as being more secure than giving online store CC details? My friends do not want to deal with paypal, but would love to accept payments if clients want to pay through paypal. I hope it makes sense. Thank you in advance.