Jay Grayson

Chief Executive Officer and Co-Founder

Surround Insurance

Jonathon (Jay) Grayson is CEO and co-founder of Surround Insurance, a venture-backed insurtech headquartered in Cambridge, MA. Surround helps digital natives find the on-ramp to insurance through personalized bundles designed around mobility, shelter, and work.

Jay was previously an executive at Liberty Mutual Insurance for 13 years where he held roles in mergers and acquisitions, investor relations, strategy, analytics, and customer experience. He is an angel investor through the MIT Alumni Angels of Boston.

Jay earned an SB degree in economics from MIT and an MBA with distinction from the SC Johnson Graduate School of Management at Cornell University where he was a Park Leadership fellow.  Jay is a first-generation Asian American and lives in Brookline, MA with his wife and two sons. On the weekend, you can find him at sunrise on a golf course.