Sasha Lawler

Sasha Lawler is the Founder & CEO of Roam, the first cancellation insurance platform purpose-built for the vacation rental industry. Roam flips the traditional travel insurance model by protecting property managers’ booking revenue from guest cancellations— finally making it possible to offer flexible cancellation policies that boost bookings without sacrificing revenue or owner trust. The result? Happier guests & owners, better margins and a future where professional managers can stay competitive.

Sasha brings over 15 years in hospitality and vacation rental tech, startup grit, and a clear vision for where legacy insurance has failed—and how embedded, automated solutions can transform the guest experience and unlock more revenue. She’s equal parts tactical and visionary—and always up for a real conversation about the future of travel, risk, and trust. 

She lives in Bend, Oregon, with her husband, five-year-old son, a vintage 1984 camper, and an unshakable loyalty to Duke’s mayonnaise.