Stephanie Usry
Executive Coach
Stephanie is an executive coach and founder working with fast-growing startups and their leadership teams. She spent a decade leading product and operations at HotelTonight, Pure Storage and Vida Health.
- Previously
- HotelTonight · Pure Storage · Vida Health
Stephanie has a rare ability to work across different leadership styles and help everyone show up at their best, whether in one-on-one coaching or guiding the team through strategic decisions. She helped us build the foundation for our executive team to run the organization well during a critical growth phase.
More about Stephanie
She helps CEOs, founders and executive teams replace ambiguous assumptions with explicit expectations: sharpening individual leader confidence, building teams that execute together, and helping companies deliver at pace. Leading product and operations taught her that the best technical strategies fail without strong human alignment.
She founded Clutch Insights, a suite of AI tools that help leaders get honest with themselves so they can be direct with each other, and runs it alongside her coaching practice. Her clients, from startup founders navigating their first leadership teams to executives at Anthropic, Uber, Google and top-tier VCs, trust her to cut through noise and build the clarity and confidence to move forward.
Based in San Francisco. CTI, ORSC (relationships and systems) and Enneagram certified coach.
Where Stephanie makes the difference
Co-founder coaching
Leadership team coaching
Explicit expectations over assumptions
Working with Stephanie through Squadra
Tell us the need
A few lines on the role and the team. We reply personally, usually within 24 hours.
Meet Stephanie
A first call within the week, free, to check the fit both ways.
Start the coaching
Sessions at your pace, for you or your leadership team.
More of the collective
Ask for an intro to Stephanie
Tell us a little about your company and what you need. We'll reply personally, usually within 24 hours.