Operator Spotlight
Strategy & Partnerships

Meet Stripe Head of Strategy & Operations and Business Lead of Enterprise Product Maia Josebachvili

Caroline Caswell

“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

This month, we chatted with Maia Josebachvili, Head of Strategy & Operations and Business Lead of Enterprise Product at Stripe. Maia’s held multiple senior leadership roles at Stripe – including Head of M&A and Investing and Head of People. Maia is active in the startup community, serving as an advisor at GV (Google Ventures) and on the Board of Directors of Brightwheel. Before Stripe, Maia was the Founder and CEO of Urban Escapes, an e-commerce travel company. She was honored as Inc’s 30 under 30, and eventually sold the startup to LivingSocial, where Maia served as GM of New Business Initiatives. She later served as CMO and VP of Strategy & People at Greenhouse. Throughout these experiences, she’s been a part of the growth journey of scaling several companies from 1 → 8,000 employees. Before her career in tech, she also had a short stint as a professional skydiver (!).

Tell us a bit about the evolution of your roles within Stripe over the last six years and what drove you toward each opportunity?

I’ve been fortunate to have the opportunity to take on a variety of roles throughout my tenure at Stripe, supporting the growth of Strategy & Operations, Enterprise Product, Professional Services, M&A and Investing, and People. While this is a fairly non-linear path, the common through line is that every role has allowed me to help Stripe navigate new frontiers. Each chapter required cross-functional collaboration and building, whether it was  strategies, products, or teams. As a founder, I’m drawn to opportunities where I can help incubate / scale functions through their “Series A/B” within the company. It can be valuable to take a startup mindset in these journeys – working through milestones like finding product-market-fit for the function (different companies need different things!), or building the leadership team needed for the next level of scale.

Earlier this year, you hosted a session for OpCo founders on strategic planning. What were a few of the key insights you discussed, and what advice do you have for early-stage founders as they think about planning for 2024?

We had a great conversation and I learned a lot from our founders as well! Three main takeaways from the discussion: 

  1. Great leadership teams build great companies. Everything comes down to people, and time and time again I’ve found that (generally), when things are going really well, you can point to a terrific leader and team. Planning isn’t just about a product roadmap or financial plan – it’s equally important to look at the work ahead and make sure you have the team that can deliver against it. This often requires planning for new leaders you need to bring on, and simultaneously being honest and clear-eyed in situations that aren’t working, then moving fast (and empathetically!) to course-correct.
  2. Invest in the foundations. It’s often easy to deprioritize the “unsexy” work in favor of the shiny projects. Most of us would rather focus on the latest new product feature versus revamping our backend systems or internal operational cadences. But, time and time again, I’ve found that building up operational debt always comes back to haunt you, and it would have been so much easier to invest earlier. This was also echoed by many of the other leaders in the conversation.
  3. Strategy is about what you aren’t doing. Most companies don’t have a shortage of great ideas, but they are all constrained by execution capacity. I’m a big believer (and I don’t think I’m alone here!) that focusing people on a few big priorities yields better results than spreading everyone too thin. While it’s painful to say “no” to great opportunities, sequencing the work ensures a sustainable pace and the most productive focus for your team – ultimately leading to better outcomes.

How has your board role at brightwheel strengthened your operating chops?

One of the leadership skills I’ve come to value most is the ability to ruthlessly prioritize. The best leaders I’ve worked with have an uncanny ability to identify the most important things, even when they aren’t obvious, and focus their efforts there to really move the needle. The nature of being on a board is that you’re not in the day-to-day of the operations, so it’s even more important to make sure that the time you’re spending with the leaders has the highest leverage. Working with the terrific Brightwheel leadership team has helped me hone my focus on prioritization, because I want to make sure that every minute we spent together was truly impactful for them.

Describe one pivotal moment in your career that was truly defining for you in one way or another - an opportunity that changed your life or a moment where you recognized defeat and changed course.

Looking back, my career is defined by a set of non-linear roles and opportunities. And while I still get that lump in my throat every time I jump into new territory, I’ve built out a bit of a personal playbook on how to do it. 

The first time I took on a new leadership role, however, I didn’t have a blueprint. I was VP of Strategy and People at Greenhouse, and jumped into an interim-turned-permanent VP of Marketing role. There were bumps in the beginning, and a few moments (okay, a lot!) where I questioned if I could do it. Not surprisingly, my imposter syndrome was at an all time high – how do you create a marketing plan and thoughtfully allocate millions of dollars to campaigns if you’ve never done it before? But I leaned into the discomfort and humility, partnered with the team of experts, sought out a personal “board of directors” of leaders I admired to help and mentor me along the way, and fully embraced the learning mindset.

Since then I’ve taken on many new “first-time” roles, and been fortunate to work with terrific teams along the way. What I’ve learned – 

  1. Lean into the discomfort and humility. Growth comes from stretching, which means stepping outside of our comfort zones and embracing humility. Check yourself regularly. If things are feeling too routine or too comfortable, it’s probably time to think about the next moment of stretch.
  2. Oftentimes, the biggest growth opportunities are lateral. That stretch doesn’t always have to mean climbing the next rung on the ladder. I’ve personally found that I’ve experienced the most growth from the lateral movements on the jungle gym, adding new skills to my toolkit. 
  3. Surround yourself with great people. Teams are everything. When I look back at each of these pivotal moments, what stands out most are the amazing teams I had the opportunity to work with.

What’s one piece of advice you would give to yourself 10 years ago, if you had the opportunity? 

Optimize for working with amazing people on great opportunities and don’t overthink the rest – just jump. It’s okay if you don’t know exactly where each adventure will take you. Just keep working with great people and focus on having impact — the rest will work itself out over the long run :)

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