Natalie Gray is the Co-Founder and Head of Product at Cover, the insurtech company that allows anyone to insure anything through a mobile app. The founding team are Y Combinator 2016 alumni and just closed a $16M Series B round, bringing their total funding to $27M.
Prior to Cover, the team co-founded Stylekick–a mobile app for fashion e-commerce which was acquired by Shopify. Gray and her team started working on Cover as a pet project and the rest, as they say, is history.
Do you often go to books whenever you have a question? Do you actively seek these technical books for answers depending on the situations you’re in?
Yes –I tend to choose books based on the challenges I’m facing at any given moment.
Skimming is particularly helpful for dense technical books. I’m also pretty comfortable with abandoning a book if I feel like it’s not valuable to me. Instead of thinking, ‘This book is now my Bible and I’m going to follow it to a tee,’ I try to tease out the bits and pieces that are most relevant to me.
Because you’re running into a time scarcity, what do your reading habits look like?
I read about five books at a time. I like to be able to switch topics frequently because I feel more engaged that way. I’ll normally read technical books in the morning when I have more tolerance to focus and I’ll switch to fiction in the evening to wind down.
I’m 100% team e-reader over physical books, largely because it helps me improve my reading comprehension. I like the fact that I have no concept of how far into a book I am so I can just focus on the words in front of me. I’ve gotten into the habit of having it with me at all times, too, so if I have 5-10 minutes of idle time randomly, I can get into any book that catches my eye.
What was the transition like from your full-time job to being a full-time entrepreneur?
When you have a full-time job, the steps to success are clear and well-defined–you can see a path ahead of you. When you switch over, none of those things are there. You make the rules and define the problems as you go. It was daunting to go into the unknown with our first startup but by the time we started Cover we knew what the journey from the idea to seed funding looked like. It was less scary taking that step from a full-time job to entrepreneurship the second time around.The same work we had plugged away at for two years with Stylekick was completed within only 3 months at Cover.
What was your experience getting into YC? You mentioned that you applied multiple times before. What changed this time and how did you stand out?
With Stylekick, we applied, interviewed and were rejected three times. E-commerce had its moment before we came in and the investment capital just wasn’t there anymore.
With Cover, we applied once and were accepted with an MVP product that had only four buttons and a handful of sales. We were there at the right time for insurtech: right when the space was heating up and people were looking to invest massive amounts into the industry.
When we were accepted, we had only a couple weeks to choose whether or not we wanted to take the opportunity. Three weeks later, we had left our jobs and moved to California. I’m really glad we made that decision. I think we all are.
What were the two learnings you had at YC that were really helpful to you specifically and the things you do today?
Honestly, the entirety of YC was life-changing for us. The access to resources and expert advice you gain is incredibly valuable.
I’d say one of the major things we learned was how to effectively solve problems on a quick two week cadence. We got into the nearly constant rhythm of identifying problems, executing solutions and then moving onto the next. This taught us not to linger on the same problems for too long so we could continue progressing.
I would say the second most important takeaway was learning how to tell our brand story. Throughout the program, I could really see the difference that a clear narrative could make when you have such a short amount of time to pitch your business.
What’s the best and worst piece of advice you’ve received over the years?
Know your problem. This is so important in product design because there are infinite solutions, but you have to pinpoint the one problem you’re solving for before you can create a truly tailored solution.
I don’t know if I can recall a “worst” piece of advice since I’ve become good at filtering it out over the years. As a new entrepreneur, you tend to give every piece of advice that comes your way an equal weighting. But really, accepting advice becomes an exercise in hearing another perspective and teasing out the nuggets that make the most sense for your business.
What’s a low light or “I messed up moment” that was important to you and why?
When you’re a small team servicing only a few thousand users, you can ship product aggressively. Cover is now at a size where even small copy changes can have a large impact on our business. About a year ago, I shipped a copy change to 100% of our audience because it was just a copy change–no big deal, right? On that day, our customer response rate went down 30%…whoops!
As we’ve scaled, every change–no matter how small–is tested with a small percentage of customers first before we ship the change to our entire audience. That was a pretty important lesson and I’m glad we learned it early on.
Do you test the feedback slowly as you receive it from users?
Yes–with any change, regardless of whether it’s based on feedback or our own experiment. We release new product changes to 10% of our audience and then let it run for a week or two. If the results are positive, we increase to, say, 25%. We keep doing that until the test is statistically significant and then switch over to 100% rollout. We also wrap all our changes in features flags which means if the change sparks a negative reaction, we can turn it off quickly.
Meta on meta, it’s for designers who are now hiring a team. This book was really helpful in figuring out how to hire and identify skill levels, how to vet candidates, which type of model we wanted to follow for the organization. It was a really excellent read...(Natalie's Notes)
Lean Analytics is a good read for new founders learning how to properly time and execute their ideas. You reach a point where it’s no longer just about this massive original idea or innovation; but more so analyzing results, and quickly iterating. (Natalie's Notes)
Written by a very prominent startup and CEO coach, it’s an excellent summary going over everything that you would need to know from establishing HR to scaling a team, improving personal productivity and cultivating office culture. (Natalie's Notes)
Be warned: this is some hardcore science fiction but it was also an excellent book for leadership, communication styles, and personal growth.
This book had a bunch of simple pieces of advice that I’ve used to help me solve problems day-to-day. It does get pretty philosophical (and sometimes melodramatic) but it was a worthwhile read, for sure.
Lastly, To Kill a Mockingbird. I just love this book. It’s such a classic and I think it teaches a lot about compassion and leadership during a very formative time in the US.
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