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  • Writer's pictureSandy Jiang

FinTech Female Fridays: Meet Co-Founder at Cover, Natalie Eva Gray

"Weird cool, not weird cringe. "Natalie might see herself this way.

Natalie Gray is co-founder and Head of Product & Design at Cover, a modern purveyor of insurance, focusing on making property insurance fair and accessible for Cover's members across the US. Natalie is responsible for setting the vision for Cover's consumer products, product design, as well as branding.

Natalie started off her career working for fashion brands during grad school at NYU. This path led to the founding of her first startup in 2013, Stylekick, which was a style curation, and shopping app. Stylekick's leap into mobile was well-timed and after a few years, they were acquired by Shopify where Natalie was part of Shopify's Design and Product Growth Teams. In 2016, Natalie joined Y Combinator with her second startup, Cover. Cover adopts a mobile-first approach as an insurance provider. Cover services all 50 states and distributes through thousands of independent agents across Texas and California. On the education side, Natalie has a Bachelor of Commerce and a BA in Mathematics from Queen’s University in Canada. Natalie is a Y Combinator and Forbes 30 under 30 alum.

Natalie loves challenges and uncertainty, that's why she rarely needs to be motivated or encouraged to start a project. "To be honest, the start is always my favorite part of a project. Everything is new, interesting, and in need of exploration. It’s always fun to bust out the whiteboard and post-its for a whiteboarding session. If I do need encouragement it’s more likely towards the end of a project where unexpected problems can come up, scope creeps, or just making deadlines. "

When asked how she is impacting Fintech, Natalie's answer is sincere and simple. "Insurance is not the most glamorous space but it is a meaningful amount of someone’s after-tax income. You have to have it to drive, rent an apartment, or own a home. At Cover, we’re working on creating insurance products that are affordable, accessible, and cater to an underserved market. Financial empowerment is for everyone. " She says. "At Cover, I’m very lucky to spend my time solving problems with a very dedicated and diverse group of people. " She adds.

More on Natalie

Current location: I’ve been living in San Francisco the past 6 years.

Hometown: I’m originally from Toronto.

Favorite hobby: My favorite hobby is reading and hanging out in the sun.

Favorite part of your day: My favorite part of the day is the morning. Those first few hours after waking up I can accomplish anything. Also right after the sunset. Natural mood lighting and it’s quiet.

Do you have any productivity hacks?

  1. My brain is a race car, not a minivan. I try to store as few facts and reminders as possible in my head. As soon as I think of something I write it down so I don’t have to keep carrying it. Like a computer, the less brain power is used as storage than the more that’s available for creativity.

  2. I can do anything hard for 30 minutes. I’m a bit of a procrastinator so setting a timer kind of takes the pressure off. I don’t have to finish anything. I just need to put 30 mins of energy towards it. Usually, it’s never as hard as I convince myself it is and now I have a benchmark of what it will take to complete. It’s like don’t worry about getting to the top of the mountain just start walking.

  3. Take care of your future self. I think about my future self as a different person. She’s someone I care about and I want to make sure she’s set up to succeed and I do my best to help her out. It can be little things like prepping the night before to make my morning routine easier for her, setting reminders, or just setting boundaries. I know it’s weird lol.

Media recommendation: I don’t really have anything consistent that I refer to daily. I read a lot of books where I’m continuously cycling from non-fiction, history, science fiction, design. Sometimes, and this is unintentional, what I’m reading will have some relationship to current events which is cool. As long as I have the motivation to put interesting things into my brain I’ll pretty much consume whatever to keep that train moving. I am a big fan of Libby and Goodreads.

Daily diary

I’m a big fan of trying to match time management with what my brain is able and willing to do in the present time. I think this makes me productive at all times whether I need to think deeply or do more autopilot-type tasks like answering emails. There will always be things to do but only so many hours in the day. If I really can’t do anything I probably need to sleep, which more often than not is the most productive thing I can do.


6:30 AM - 8:00 AM: Wake up. I try to really listen to my brain and my body. I will do varying combinations of reading in bed, making breakfast, walking my dog, and getting ready for the day.

8:00 AM - 9:00 AM: I start off my work day with team standups where I get a quick pulse check from engineering and design.

10:00 AM to 11:00 AM: Once a week our exec team will meet to discuss the most important opportunities or challenges for the business.

4:00 PM - 6:00 PM: At this point, I need to unplug and get a break from the desk. I do my best to get out of the house every day even if it’s for boring stuff like grocery shopping, or errands.

6:00 PM - 8:00 PM: Back to work. The house is pretty quiet and it’s ideal for me to do my deep thinking work. Writing, designing, learning, or prep for the next day.

8:00 PM - 9:30 PM: Dinner and hang out at home or maybe meet up with some friends for a drink. Mostly just winding down for the night.

9:30 PM: I go to bed pretty early these days. I’m also an avid reader and this is usually when I get most of my pages to read.


My morning routine is pretty consistent but I avoid any kind of schedule for the rest of the day. I would say I’m still fairly productive on weekends but I need a break from the scheduling, device use, and just the rigor of the weekdays. Less work stuff more so looking after myself, my environment, and general adulting.

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