Maia Josebachvili’s life and career have been nonlinear, spanning continents, cultures, and coasts, with roles ranging from founder and CEO, to CMO, to senior executive roles leading people operations, corp dev, and product management. Today, Maia serves as Stripe’s Head of Strategy and Operations and Business Lead (GM) for its enterprise product and is one of the company’s key executives preparing the business for its next chapter.
With an early childhood in Argentina and Spanish as her first language, Maia immigrated to New York City at age six. She earned her mechanical engineering degree at Dartmouth’s School of Engineering before launching her first startup, Urban Escapes, a business-to-consumer travel company. In that early founder phase, Maia found that startup life and skydiving were great outlets at the intersection of autonomy and adrenaline. Over that period, she sold her startup to LivingSocial — and became a seasoned skydiver, eventually logging more than 750 jumps out of airplanes.
Maia’s early success as an executive at Living Social and then at companies like Greenhouse, where she excelled in radically different roles, including VP of People and CMO, was proving ground for her current gig at the epicenter of the startup ecosystem. Maia has layered her founder experience with extensive executive and life experiences, most recently with 5+ years across leadership roles at GV portfolio company Stripe. In addition to her day job, Maia advises several startups, with multiple board roles.
Today, I’m incredibly excited to formally welcome Maia as GV’s newest Advisor, coaching our portfolio company founders on high-agency culture, founder mindset, scaling organizations, and growth.
I recently sat down with Maia to discuss leadership lessons, perspectives on scaling, and how a skydiver’s mindset applies to high-growth startup teams. At GV, we often talk about pattern matching, and one of the patterns we see most often in successful startups is the concept of “high agency” leadership. Having gotten to know Maia over the past couple of years, she embodies this approach. She maintains a constant owner’s perspective, with the confidence to creatively solve problems, the resilience to persist through the hard parts, and the charisma to influence broad audiences informally along the way — traits we see in the founders we work most closely with.
This concept of high-agency leadership is also innate to Stripe’s culture: Not only does the company encourage it, but the team intentionally fosters an ownership mindset. In Maia’s words, “I think of myself as a forever founder. I’m just doing it at a larger company.”
Maia advises early-stage founders to think about building foundational systems that apply to the specific stage and scale of their organization. “Creating an environment where people can do their best work at 50 people and 150 people looks very different,” she cautions. She encourages founders to constantly reimagine a startup organization and embrace adaptability: “Scaling a company is a living, breathing organic process.”
Maia has an uncanny ability to jump into any situation — both figuratively and in a quite literal sense, given her skydiving expertise. We’ve often compared notes on the parallels between “jumping” and startups, informed by her impressive 750 skydives and my early career experiences as a military officer and paratrooper, traversing dozens of countries and through combat zones while leading teams under pressure. “When you skydive,” she explains, “you’re often in a plane with people you just met. And here you are asking a stranger for a pin check (a pre-jump safety procedure), which is literally placing your life in their hands.”
In these situations, you very quickly learn that fostering high-trust interactions (and teams) is essential, not just to success, but to survival. Maia drives that approach through her leadership style, defaulting to high trust with new team members from day one. She shared, “I’ve consistently found that starting relationships from a foundation of high trust helps create the most rewarding and impactful environment for everyone.” Studies indicate that employees working in high-trust cultures experience less burnout, more empathy, and overall work satisfaction.
Our conversation concludes with Maia’s advice on how founders can adopt a high-agency mindset: “The thing about being a founder or working for a startup is that you have to choose it. It’s not an easy path; it’s hard to be a founder. If you’re not passionate about the mission, about a decade or more of hard work, you shouldn’t do it. There is a level of agency and commitment as a startup founder that once you jump — you’re jumping. There is no turning back.”