This week, the Bowery Capital team hosted Jeanne DeWitt, Head of Sales for US and Canada at Stripe, to discuss “Team Structuring In Transactional Sales Organizations.” Stripe is a technology platform that developers use to build internet businesses. Thousands of businesses – ranging from startups to Fortune 500 companies – rely on Stripe’s software tools to securely accept payments, expand globally, and create new revenue streams. Stripe users include Twitter, Kickstarter, Shopify, Salesforce, Lyft, and many more. On the podcast, Jeanne and I begin talking about her background from Google, Dialpad, and now Stripe and specifically how those organizations were designed. We then moved on to describe what we all mean when we talk about “transactional” sales organizations so the listeners could understand our overall point of view. From that point, we covered how Stripe is designed from an organizational standpoint and how it differs in terms of SDRs (none), AEs, and CSMs. We also talked a fair amount about other organizations and thinking through when to move away from “self-serve” to something like transactional selling. Jeanne also gave the listeners some points of view on how she and the founders approached sales two years ago (remember Stripe was very successful with their self-serve model), noting how this conversation can go very right or very wrong when your self-serve product is high velocity and working well. We then talked about what metrics are necessary to move from self-serve to anything more upstream from a selling standpoint. When to hit the gas and when to maintain the current state is really important and Jeanne gave great tips from her pattern recognition over a long career. She feels that people tend to move up too early and talked a lot about the math necessary to do this. We close on hiring and celebrating wins in organizations that are primarily transactional. Overall, it was a wonderful podcast and Jeanne has had an exceptional career with lots of knowledge to share. Jeanne DeWitt is the Head of Sales for the US and Canada at Stripe. Prior to joining Stripe in 2016, she was the Chief Revenue Officer at Dialpad. Before that, Jeanne held multiple sales leadership roles at Google, including serving as Director of SMB Sales for North & Latin America and Head of Google Apps SMB Sales for Japan & Asia Pacific. Jeanne studied Markets and Management, as well as French and Spanish, at Duke University before going on to receive her MBA from Stanford University.