In the past decade, I’ve been a company’s early sales hire and also served as a VP leading a 100-person global sales team. So whatever challenges your startup is facing as it scales and matures its sales org, I’ve likely lived through them, recently. As I like to tell founders, my startup experiences are too fresh to have faded — at the time of this writing in March 2021, I can say that I had a quarterly number just one quarter ago.
But if you wind the clock back to the beginning of my career, it wasn’t at all clear that I’d end up in this role. I’m a first-generation American who’s from the Midwest. After college, I landed in the world depicted in “Moneyball,” working on player development and baseball operations for the Cleveland Indians. In my next gig, I came to San Francisco for the very first time to work at Bain, partnering with big companies that seemed very far removed from early-stage tech. I spent the next five years with my nose to the grind, sharpening my sales chops, chasing my numbers and building out teams in startup settings.
But when I look closer, I can spot the throughlines. Baseball may be leagues away from venture — you’ll have to excuse the pun here — but spotting hidden minor league talent and coaching them up to the majors isn’t all that dissimilar from betting on early-stage founders and partnering with them on their path to IPO. (They both require patience and tolerance for long feedback loops, too — after I’d already left my role at the Cleveland Indians, I was proud to see some of the players I helped draft in 2007 take the field for the World Series in 2016.)
Partnering with the C-Suites of Fortune 50 companies at Bain taught me how to work across numerous spaces — many unknown to me on Day 1 — and how to dive deep into the legacy tech that tomorrow’s scrappy startups will be taking on. Scaling Stripe’s sales org taught me how to obsess over the customer, which in our case, happened to be startup founders looking to figure out their revenue models. And sitting on Mixpanel’s executive team as VP of Sales & Services gave me an up-close look at the cross-functional challenges leaders at every growing org face.
Whether it’s figuring out how to develop their ideal customer profile, or how to transition from founder-led sales to their first outside sales hire, my passion lies in leaning on these experiences and rolling up my sleeves to help product-focused and technical founders in those crucial early days. As an angel investor before joining First Round, the parts I loved most were when I felt I was truly pitching in and getting my hands dirty, from building out pipelines and defining revenue goals, to helping to craft product messaging and structure pilots.
This is what appealed to me most about the chance to join First Round — our laser focus on helping founders get from zero to one, whether it’s with the first version of the product, the first set of customers, the first hires or the first couple million in revenue.
What also stood out is that my impression of the firm wasn’t formed in the months-long interview process I went through. It was formed over years of reading the First Round Review, through taking part in Fast Track as a mentor, and of course, through being a part of the Spring 2019 cohort of Angel Track. Through Angel Track, I saw the level of detail and care that went into every event. I remember looking around as I sat in a room with 15 other incredible amateur angel investors while we listened to Elad Gil, thinking about what a unique chance it was to pick his brain and learn how to bring more rigor to my own investment decisions.
I so valued being a part of the First Round community that when I learned they were looking for a new partner in 2020, I immediately threw my hat into the ring. After I got the offer and I quietly started sharing the news with people, I was struck by how everyone I told had a story of their own — a tale about how someone on the First Round team over-delivered, or how one of the team’s programs helped them get from one place to another. It was undeniably special to hear founders and operators talk about this team in a way that matched my own experiences.
My mom always said, “You are an average of the five people you spend the most time with.”
Throughout my career, I’ve come to see just how much wisdom there is in her words. On the sales teams I’ve run, compensation has always been tied not only to individual performance, but a team target too — and at Stripe, my teams never missed their numbers. Venture is a team sport as well. Whether it’s how we evaluate investments as a group or hand off opportunities to whoever has the most experience in the space, the collaborative culture at First Round makes us better partners to founders.
So does the way we lean into the power of community. At the center of First Round is this idea that we aren’t going to just sit on all this knowledge we have — we’re going to open up, try to share it at scale, and help more people build better companies.
The founders I love working with take a similarly purpose-driven approach in their own respective industries. They’re resilient, adaptable, ambitious, and most importantly, customer-obsessed. I invested early in startups like Rimeto, Coda, Snackpass and Stytch — teams tackling everything from workplace collaboration to food delivery and user authentication — not just because of my own theses in these spaces, but because of my desire to partner with the incredibly talented founding teams. I firmly believe that these teams could be successful at whatever business they chose to build.
Finally, there’s nothing I love more than a founder who’s been underestimated. Talent is evenly distributed, but opportunity isn’t. There are a million things that we need to take on to make the world of startups and venture more inclusive and representative of the world we live in. I hope I can play a small role in opening doors and helping more founders hit it out of the park. In my view, it doesn’t get any better than that!
