Surround Raises $2.5 Million To Continue Its Pursuit of Building “Insurance Built Around You”


Boston-based Insurtech Plans Include Expansion Outside Massachusetts in 2023

Surround Insurance | Massachusetts
Kate Terry and Jay Grayson 

Surround Insurance is widening its circle of influence with the close of a new round funding in which it raised $2.5 million. The insurtech start-up says it will use the cash infusion to expand both Surround’s product and distribution footprints. Currently available in Massachusetts, Surround says its offerings will available in eight additional states in early-2023.

“Jay and Kate are focused on solving problems for consumers who need insurance that’s built around their lifestyle instead of their assets – insurance that isn’t easily accessible today,” said Jason Allen, Portfolio Manager, Impact Investments at MassMutual. “MassMutual’s relationship with Surround extends back to our collaboration through the MassChallenge FinTech program, and this investment represents our continued confidence in Surround’s future and vision.”

The seed round was led by MassMutual through the MM Catalyst Fund with new investor Aperture VC also participating in the round, along with existing investors Newark Venture Partners and Cameron Ventures.

As outlined in its official launch on Agency Checklists in 2020, Surround was co-founded by Massachusetts insurance veterans Jay Grayson and Kate Terry to address a $10 billion opportunity for consumers getting started with insurance. Surround has designed its experience around transition moments like leaving the parental nest for college, establishing life in the city, or making a first-time car purchase.

Drive-Rent is Surround’s most popular offering thus far

Surround’s initial set of products are designed around emerging risks such as driving rented or shared cars and freelancing for extra income. Surround helps first-time insurance purchasers with in-the-moment advice and products built for an asset-lite lifestyle. The company’s most popular product is the Drive-Rent bundle which includes portable auto insurance for non-car owners plus apartment insurance.

“Lifestyles of young adults in their 20s and 30s are changing rapidly and dramatically,” said Jay Grayson, CEO and Co-founder of Surround. “They are moving, living, and working in ways never imagined by traditional insurance, and we’re helping them navigate a confusing and complicated set of risks. Oftentimes, our customers are buying insurance for the first time, so we have the perfect opportunity to win them early and then keep them for life.”

Surround’s insurance platform provides a consumer-centric experience around three core product areas:

  • The Customizer – Match your lifestyle to the right insurance for you
  • Insurance Advisor in Your Pocket – Connect with a live agent for expert advice, not a bot.
  • Insurance Starter Packs – Get a personalized insurance bundle in less than four minutes

The Company distributes through independent agents, partners such as Nerdwallet, and directly to consumers through the Surround Insurance Agency.

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