Suggestions
Jake Stern
Founding Sales at Plain – customer support for B2B businesses
Jake Stern is a prominent figure in the fintech industry, currently serving as the Founding Account Executive at Plain, a company focused on simplifying financial services. His career began at Plaid, where he was the first New Business Associate, responsible for outbound sales and developing new business opportunities, particularly during Plaid's expansion into Canada. His role involved engaging with startups and enterprises to help them integrate Plaid's services into their operations, showcasing his consultative sales skills and ability to communicate complex technical solutions to diverse audiences.12
Stern's educational background includes a degree in economics from Brown University, where he also initiated an entrepreneurship program called Innovation Dojo. This experience reflects his passion for innovation and collaboration in business settings.1 Prior to his role at Plaid, he gained valuable experience as a field organizer on the 2016 presidential campaign, which honed his skills in team leadership and strategic outreach.1
Outside of work, Jake is known for his adventurous spirit, particularly enjoying motorcycle riding and exploring new places.1 His professional journey illustrates a blend of technical knowledge, sales expertise, and a commitment to fostering innovation in financial technology.
Highlights
After 7 incredible years, I’m excited to share that I am moving on from Plaid and making a (very) dramatic phonetic shift by joining Simon and Matt to found Sales at Plain!
When I joined in 2017, Plaid was a 50 person startup out of a small office in San Francisco supporting 100 customers. I had no idea that I was signing up to help build a generational business with 8,000+ customers, 1,000+ employees, and a global presence. I feel incredibly lucky to have been able to work with and learn from some of the greatest startup leaders in the world. Thank you to Zachary Perret, William, Paul, Kate, and Charley for taking a chance on me all those years ago. My sincere gratitude as well to all of the colleagues and mentors who have helped me along the way like Jack, Emerald, Sam, Matt, Lauren, Keith, Dan, Eric, Adam, Brendan, and Brian.
One of the things I’ve learned over the years is that building great B2B businesses requires meeting customers where they are, and speaking with them where they prefer to communicate -- oftentimes in channels like Slack. But with client conversations taking place across more and more mediums, it's increasingly difficult for platforms and SaaS companies track and resolve issues that require involvement from multiple internal stakeholders.
Over the past few months, I’ve been amazed by the level of enthusiasm about Plain from the global technical support community. When I met Simon and Matt and heard about their vision to build the best support platform for B2B companies, I felt like there was an enormous opportunity ahead.
Most importantly of course, the opportunity for play on words was too great to pass up :)
Excited for what’s next and please excuse my inevitable typos to come!
