.png)
In this Q&A, Viviane shares how mentors shaped her path, why she believes the best operators are proactive, and what makes OG so unique.
Viviane Crosthwaite is the VP of Operations at Esper, where she oversees everything from finance and legal to HR and strategy. A longtime operator and former tennis pro, she recently began building her own startup—an AI-powered HR co-pilot to simplify administrative work for operators. She also leads the OG Denver chapter, where she brings energy, creativity, and a deep commitment to building community.
In this Q&A, Viviane shares how mentors shaped her path, why she believes the best operators are proactive, and what makes OG — and especially the Denver chapter — so unique.
Could you start by introducing yourself and sharing a bit about your role and background?
I'm currently the VP of Operations at Esper.
Like many operators, I wear a lot of hats—finance, accounting, HR, legal compliance, strategy, you name it. I recently started working on my own startup, an AI-driven HR co-pilot for operators to handle basic admin tasks across software tools.
Fun fact: I used to be a tennis pro!
What role have mentors, advocates, and peers played in your journey?
They’ve been crucial! I wouldn’t have progressed without learning from others, even if it wasn’t in a formal mentorship setup. My former boss and mentor, Marcos Torres—also an OG member—was especially influential. Now, being able to reach out to him and others on Slack through OG has been invaluable. As operators, we don’t work in isolation; we’re a community that’s constantly learning from one another.
What do you think separates good operators from great ones?
Great operators solve problems before they appear, while good operators are ready to solve issues as they come up. Both are fantastic problem solvers and critical thinkers, but great operators help shape the company’s strategy by anticipating future challenges and acting proactively.
Any advice for first-time operators?
Do every job you can get your hands on. My career succeeded because I’ve done it all—from office management to HR, finance, and contract management. It equipped me with a broad skill set and a mindset for tackling diverse problems, which is essential in operations.
What makes the Denver chapter special?
We’re a creative, fun-loving bunch. For example, during the OG Summit, a playful comment in the group chat led to the entire Denver chapter showing up in full costumes for the end-of-summit celebration. We embrace our weirdness!
What’s your favorite thing about the OG community?
The breadth of experience and industries that we touch.
If you have a question or you want to find a mentor, or a job, or anything like that, this network is very powerful. It’s amazing to have a community where people truly understand what being an operator means.
Any advice for someone thinking about joining OG?
Do it.
Networking is key to career progression, learning, and growth. OG gives you access to a top-tier network.