12 Qs with Kate Stillwell, Founder & CEO of Jumpstart Insurance

4 min read
October 20, 2021

12 Questions with Kate Stillwell

Welcome to 12 Questions, a Q&A series where we pose the same set of 12 questions to intriguing folks at the intersection of insurance, risk management, commercial real estate, and digital innovation. 

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This week, we chat with Kate Stillwell, Founder and CEO of Jumpstart Insurance.

1. What is the most interesting idea you’ve encountered in your world lately?

What if “insurance” as we know it – as a separate category – disappeared? No one seeks to buy insurance for its own sake, but only in the context of some other valuable (health, jewelry, etc.). What if insurance was never a product on its own, but only and always embedded in the transaction or purchase of the thing the person wants? Homeowners’ insurance embedded in a mortgage, auto insurance embedded in the auto purchase…not just “one stop shopping,” more like fully-inclusive pricing. The idea is akin to the new trend of top fashion brands taking responsibility for the full life-cycle of their products – when you’re done using them, you can send them back to the manufacturer free of charge for the maker to recycle them for zero-waste production. Likewise, by virtue of selling you an automobile or financing a home, the price of the product includes all potential costs related to that object over its lifetime, including its damage or loss.

2. Where do you think no one is looking right now?

What if we re-imagined a new generation of mobile home parks to suit a nomadic, free-spirited lifestyle? After a year of widespread working-from-home, there’s this phenomenon, particularly among younger people, to re-balance their work time and reconsider where they want to live – which may be many places. Next-gen “mobile home parks” (they would need a different name) would not be for “hippies” or for limited-income folks, but for the “burning-man” crowd – professionals who newly prioritize being closer to open space but who nevertheless need good internet. A space to find spontaneous community while seamlessly interweaving of work and life.

3. If you had a magic wand, what would you change about your industry?

The public’s perception and preconceptions about the insurance industry. There are a lot of factors that give insurance a bad reputation and I would magically eliminate all of them so that the average consumer believes insurance is there for them, not against them.

4. What’s the most rewarding part of what you do?

The mission. To get money in people’s hands at the time when they need it most. Imagining the stories of customers being able to stay in their homes, help their neighbors, plow back in their communities, that’s what keeps me going.

5. What do you envision the next 12 months will bring?

I think a large swath of everyday folks will continue to reshuffle their priorities, leading to continued froth and frenzy in the housing market, particularly in previously-less-appealing locations: for example, rural property with intrinsic natural beauty.

6. What’s your favorite building?

Soooo many to choose from. With my background as a practicing structural engineer, I’m particular to buildings where the structure is explicitly expressed in the architecture. One example is the Raleigh-Durham airport terminal. The enormous roof trusses are like floating sculptures, and the mixture of wood and metal, the mix of large and small diameter posts, adds to the visual richness while also hinting at the structure of early biplanes.


I also love the Marin County Civic Center by Frank Lloyd Wright. It’s a jewel amidst stunning natural surroundings. 

7. Please dispel a myth or misconception about your work.

Insurance is not as complicated as it’s made out to be. There is regrettably a perverse incentive for agents and carriers to obfuscate insurance. Furthermore, carriers and agents tend to hold arrogant assumptions about the level of intelligence of insurance buyers. But most customers understand more than we give them credit for. A parametric product for hurricanes launched recently on the island of Dominica is targeted at farmers and small businesses. There are a wide variety of product options available. The product developers assumed most customers would choose the simplest product, but the overwhelming majority have selected the most sophisticated options. They understand their risks and appreciate the product transparency – even though the triggers and limits are complicated, they get it.

8. What are the tools, apps, or gadgets that you just can’t live without?

A miniature silicone spatula. Who knew the multitude of uses it would have – both inside and outside the kitchen!?!

9. What’s your biggest pleasant surprise related to remote work?

Being around for spontaneous moments with my family members, especially my pre-teens. They don’t always want to talk to me on “my” schedule, so being around more often lets me be available on “their” schedule. It’s like the “water cooler effect” but at home – conversations that wouldn’t occur if they had to be planned.

10. What’s your favorite productivity tip for staying motivated and getting work done?

Block two half-days per week to work on the “big rocks” and turn off all notifications during those blocks of time. Save up the “little rocks” and get them done during little snippets of time – waiting at the soccer field, 20 minutes between meetings, the last half hour of the workday, etc.

11. What or who do you read/watch to keep informed?

My current inspiration is the book HumanKind by Rutger Bregman. It contradicts the natural tendency to be suspicious and sarcastic, and points to real evidence of the human goodness in all of us throughout history.

12. Please nominate folks who should answer this next.

Thank you to Mark Cravens, Principal at Cravens Consulting, for nominating Kate for 12 Questions.

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