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Natalie Gray on the TechTO stage

Natalie Gray

Product, Re

InsurtechSan FranciscoOn TechTO stages since 2018

Natalie Gray co-founded Cover, the Y Combinator insurance startup she built with the same partners behind fashion app Stylekick. She led product and design there from 2016 until Cover wound down in 2022, and now works on product at Re, an onchain reinsurance protocol. She spoke at TechTO twice in 2018.

On the TechTO stage ×2

First seen on the TechTO stage in 2018. Every talk is searchable — ask the archive about Natalie

In their words

Jargon is not a replacement for helping your customers understand. Your copy should be written for them — not for yourself, not for your investors, and not for the people in your industry.

TechTO, Oct 2018 · watch at 4:16

It was truthfully up to me to become that expert, because regardless of who you're talking to — customers or investors — they won't give you that benefit of the doubt. You have to do it for yourself.

TechTO, Oct 2018 · watch at 7:37

Geico spends a billion dollars per year on brand awareness. So how do we as startups compete with not having such deep pockets? We have to design for trust.

FintechTO, Jul 2018 · watch at 5:53
A few quotes can’t cover everything Natalie said on the TechTO stage. 1,600+ talks are searchable.Ask about Natalie

Around the web ×2

Quick answers

What is Natalie Gray known for?

Co-founding Cover, the mobile-first insurance startup that went through Y Combinator's W16 batch and raised $27.1 million. She was Cover's co-founder and head of product and design. Before that she co-founded Stylekick, a fashion shopping app acqui-hired by Shopify.

What did Natalie Gray do before Cover?

She graduated from Queen's University in 2009 and moved to New York to work for a fashion brand, then returned to Canada and co-founded Stylekick, a mobile app selling high-end fashion. Stylekick was acqui-hired by Shopify, where she worked on the Design and Product Growth teams.

What happened to Cover?

It wound down in 2022. Co-founder and CEO Karn Saroya said Cover had been underwriting profitably and distributing through 5,000 independent agencies, but funding and acquisition efforts were unsuccessful, and its policyholders were transitioned to another insurer.

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Maintained by TechTO · facts sourced and dated · last reviewed Jul 16, 2026