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Surround Insurance

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Insurtech building modern insurance products for urban lifestyles

Cambridge, United StatesFounded 2018Fintech
Valuation $10–25M Last recorded · 2022
Revenue $1–10M Latest reported FY
Headcount <100 Current team size
Total funding $10–50M Disclosed equity funding
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About Surround Insurance

Surround Insurance operates as an insurtech managing general agent (MGA) focused on providing property and casualty insurance products tailored for young, urban professionals who represent a shift towards an asset-light lifestyle. Founded in Cambridge, Massachusetts, in 2018 by Jay Grayson and Kate Terry, the company was established to address a gap in the traditional insurance market, which is primarily built around asset ownership. The founders, both seasoned veterans of the insurance industry with extensive experience at major firms like Liberty Mutual, Progressive, and Plymouth Rock, identified that modern consumers who rent, share, borrow, and freelance are often underserved by existing insurance models. This insight, partly inspired by Grayson's personal realization of coverage complexities for urban bicyclists, led to the creation of Surround Insurance.

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The company's core business revolves around creating and distributing 'starter packs' of insurance. These bundles combine coverages that are typically sold separately, such as non-owner auto insurance for car-sharing and rentals, renters insurance, and professional liability insurance for freelance work. This model allows clients to acquire personalized, subscription-based insurance in a streamlined process. Revenue is generated through its role as a national independent insurance agency, distributing products through partnerships with platforms like Nerdwallet and GO, a car subscription service, as well as directly to consumers. This multi-channel distribution strategy targets consumers at key life transitions, like moving for college or starting a career in a new city.

Surround's product platform is designed for a digital-native audience, offering features like "The Customizer" to match lifestyles with appropriate coverage and an "Insurance Advisor in Your Pocket" that connects users with live agents rather than bots. This approach aims to provide expert advice and a seamless customer experience for those often purchasing insurance for the first time. The company has received significant recognition, including being a MassChallenge FinTech Platinum Award Winner in 2019 and incubating at the Harvard Innovation Labs. Since its inception, Surround has raised approximately $5.1 million in funding through multiple seed rounds, with investors including MassMutual, Newark Venture Partners, and Cameron Ventures, to fuel its product expansion. Initially launched in Massachusetts, the company had plans for national expansion. However, reports from late 2023 and 2024 indicate co-founder Jay Grayson departed the company and the company's website became inactive, suggesting it may have ceased operations.

Source: Dealroom company data

At a glance

Founded
2018
Headquarters
Cambridge, United States
Sector
Fintech

Investors

8 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Seed7 investors entered at this stage

  • Sure Ventures
  • Cameron Ventures
  • Mike Hughes
  • Newark Venture Partners
  • Two Lanterns Venture Partners
  • MassMutual Ventures
  • Aperture Venture Capital

Series A1 investor entered at this stage

Team profiled 5 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 2 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
1 countries with
team presence
🇺🇸 United States100%
1 country shown

Market sentiment

Posts on X, past 7 days

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Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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