Innovation Success Stories
Kate Terry, COO and Co-founder, Surround Insurance


Innovation is a necessary driver for change, efficiency and bottom line. At FintechWomen, we want to bring out stories of women who have taken up this challenging task successfully. What motivates people and companies to innovate? What drives them to stay the course despite challenges? How do they create commercial value from innovation? And, of course, the lessons that lie therein.

In August, we invited Kate Terry to share her journey in leading Surround Insurance along with her co-founder Jay Grayson, as it disrupts the $700bn property & casualty Insurance industry. Our hosts for the evening were the DCU Fintech Innovation Center

For the speed viewer, we have collected key ideas along with links to the original videos.


Vasilios Roussos, Managing Director, DCU Fintech Innovation Center, introduced us to Kate’s deep industry and breadth of life experience. Vasilios also spoke about how and why DCU reviewed and selected Surround Insurance to join its program. 

  Video: View introduction here

Becoming a start-up founder: Kate’s story

Kate shared the story about her journey that transitioned from education in History and Celtic Studies at Harvard University to her accidental entry into Insurance and then to entrepreneurship at Surround Insurance. Kate also introduced Jay Grayson, CEO and Co-founder.  Kate and Jay shared their experiences as we went deeper in exploring how they conceptualized & commercialized their idea. 

Back to Kate’s story: Her quest to move into to a general management role, from transition from management consulting, took Kate to the Insurance industry where she worked at Progressive, Plymouth and more recently at Liberty Mutual Insurance. She enjoyed the dynamics of consumerism and analyzing what people wanted to buy. As her career progressed, Kate realized that the highly regulated nature of the industry limited the pace of change to only incremental improvements. The pursuit to make radical changes in the industry was the shared interest that brought  Kate and Jay Grayson together, to build Surround Insurance 

Surround Insurance was founded in June of last year, and has been growing rapidly. The company’s mission is to give its members the confidence to change the world through technology-powered insurance. 

Video: Hear Kate’s career path here

Audience questions

  • How Surround uses the ideas of live-move-work to respond to changing needs for insurance as we move from an asset based economy to access based economy ?
  • The consumption of insurance, particularly the interest of corporations to find new insurance products as benefits offerings to employees.
  • The difficulty of innovation in insurance, where there is considerable regulation and law to consider.
  • The operations behind underwriting insurance in this new model

Video: Audience Q&A

A screen-side chat: Kate and Jagathi

Swapping an eco-friendly screen for the fire in a fire-side chat, Jagathi Gururajan joined Kate to dive a little deeper into the idea of innovating as a startup in a regulated industry.  

As part of MassChallenge Fintech Program, Surround worked with one of the largest insurance companies to develop a distribution channel. Kate described what it is like to work with a large institution when a startup is essentially disrupting, or enhancing their business through a new concept.

What it took from being ‘two people and an idea’ to building a product that they could take to market? Kate and Jay took turns to speak about fundraising for a regulated and licensed insurance product, stitching modular set of technologies and how important it is to stay the course – through constant reinforcement of belief, willpower and vision.

What is the short to mid-term vision for product development?  For Surround, considering that insurance regulation differs in each state, they look at growing the footprint state by state.

How did they leverage newer technologies to build their products? This is achieved through focusing on creating customer experience, while keeping in mind building back-end legacies of large insurance institutions. Jay provided the added perspective of drawing upon the  experience generated by cross-industry beacon companies like Stitch-fix that use technology to customize clothing to suit the unique style of customers; while building an adaptive insurance product for the modern urban customer’s lifestyle.

Rounding up the chat, we spoke about how Surround relied on non-traditional sources and means of funding to overcome the challenges thrown by multi-faceted regulations.