Startup Spotlight: Surround Insurance

Dec 2, 2018


Startup Spotlight: Surround Insurance

Dec 2, 2018

Meet Kate Terry, co-founder and CIO of Surround Insurance, the startup providing innovative insurance products for the modern customer!

GH: What is Surround Insurance?

We build innovative insurance products for modern life. We’re starting with products for urban professionals who are sharing, renting, and gigging.

GH: What was your Eureka moment: how did Surround Insurance get started?

My co-founder (and Surround’s CEO) Jay Grayson and I are experienced insurance executives from a Fortune 100 insurer. We both left to explore and solve problems unique to modern life. Jay took up residency in a co-working space and realized that many of the people around him were feeling the uncertainty of living in the modern economy without a safety net. That was the birth of Surround. I joined him a few months later, initially as a consultant and eventually as a co-founder.

GH: How did you build your team?

People today have choices about what they work on and who they work with. They want to be inspired to solve important issues. Insurance is a trillion dollar industry mired in centuries past. If you think about it, though, the mission of the industry is really inspiring – to put people back together at the worst moments in their lives. So, yes, we’re hiring people who are inspired to modernize insurance – our kind of insurance!

GH: What is your company philosophy driving your company culture?

We believe firmly in an inclusive culture. As a diverse founding team – I’m a woman and Jay’s biracial – we don’t look like the founders of most startups, let alone startups in the insurtech space. We believe that a diverse set of backgrounds and experiences within our team gives us more points of view, more original ideas, and more creativity. We embrace our differences so we value transparency, kindness, personal responsibility, and a can-do attitude.

GH: Startup life is full of failures and ‘make it work’ moments – can you identify how you bounced back from one of yours?

I am sitting here cringing as I think about the first few times Jay and I pitched to venture capitalists. The things that came out of my mouth…ugh! Entrepreneurship is so humbling – I’m constantly figuring out how to do things I’ve never done before. Imperfections are part of the journey. After the first couple of disastrous pitches, I reached out to more experienced entrepreneurs and investors in my network for help, asked for feedback, and practiced (and practiced!) my part of our pitch. I feel like a completely different person in front of investors now (and I’m hoping I sound like one too!).

Kate Terry, co-founder and Chief Insurance Officer of Surround Insurance

GH: What did you learn from your first customers?

We aren’t yet in the market, but we have conducted hundreds of interviews with potential customers and with independent insurance agents. One key theme we have heard again and again is how uncertain people feel in the modern economy. There’s a real sense that a moment of bad luck in a car or on a bike can lead to a spiral of losing your income, your living situation, and your future. The products we’re building are specifically addressing that so our customers can move through the world feeling confident on their journey, whatever that means for them.

GH: What has the Boston ecosystem provided you?

Boston is a great place to start a business. The Capital Network, which awarded me a Female Founder Fellowship, has been a great source of information about the process of raising capital, which is new to me, and also a fantastic place to connect with investors, other entrepreneurs, and service providers. We work out of the Cambridge Innovation Center in Kendall Square, which is a vibrant community of entrepreneurs who are both fellow travelers on this journey and willing guinea pigs as we test creative and product ideas. In general, I’ve found the Boston ecosystem to be really supportive. Nearly everyone I’ve reached out to has been willing to offer help, advice, or support.

GH: What is the Boston ecosystem lacking from your perspective?

Diversity. Only 2.2% of venture capital funding so far in 2018 has gone to all-female teams, and 12.8% to mixed gender teams. In insurtech, the space we are in, 2% of founders are female. And racial and ethnic diversity are no better. I have been the only woman in the entire office at far too many pitches and meetings. Jay and I have worked to ensure diversity by building a diverse hiring pipeline, seeking out highly qualified advisors from a variety of backgrounds, and doing a lot of legwork to find female and minority investors to participate in our seed round. We have also joined All Raise’s Founders For Change movement ( In addition to building an amazing business, I’m committed to finding ways to support and increase diversity in the Boston ecosystem.

Jay Grayson (Founder and CEO) and Kate Terry (Founder and CIO)

GH: What’s the best/worst piece of advice you were given along the way?

We met with an investor who timed our introductions during a pitch, then absolutely excoriated us for taking too long. The next morning, we pitched a big Sand Hill Road firm and introduced ourselves in under a minute. The investor we were meeting with blinked a bit, stared at us, then suggested that maybe we could explain a bit more about our backgrounds and skills. What we learned was that everyone has an opinion and while the overall arc of the feedback we have gotten is correct and reason for us to change, overreacting to a single data point is not productive.

GH: What was the best thing that happened to you last year?

Joining Surround as a co-founder! I started working with Jay as a product development consultant. Through this work we discovered that we have complementary skill sets and that we enjoy working together, so I came on board as a co-founder. I’m really an accidental entrepreneur, and I couldn’t be more excited to reframe insurance as we build Surround.

GH: What does the future hold for Surround Insurance? We live in a time of economic uncertainty for individuals. Our ultimate goal is to eliminate the pervasive sense that one unlucky moment can ruin your life. That requires fundamentally redesigning the insurance industry around people rather than things. We’re hoping to catalyze that disruption!

Learn more about Surround Insurance!

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