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“5 Things I Wish Someone Told Me Before I Became CEO of Cover,” With Karn Saroya

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Karn Saroya, CEO and co-founder of Cover. Karn is responsible for operations, business development, growth and investor relations. Cover is a mobile-first insurance brokerage that streamlines insurance shopping through an intuitive app that generates policy quotes from […]


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Karn Saroya, CEO and co-founder of Cover. Karn is responsible for operations, business development, growth and investor relations. Cover is a mobile-first insurance brokerage that streamlines insurance shopping through an intuitive app that generates policy quotes from over 30 carriers in mere minutes. To date, Karn has raised $27M for the company through its seed, Series A and Series B rounds. He is also a Y Combinator Fellow and Alumnus.


Thank you so much for joining us Karn! Can you tell us the story about what brought you to this specific career path?

Istarted my career as a management consultant with Oliver Wyman which puts you on a very traditional career trajectory. I learned a lot there and I’m grateful for the experience, but I wasn’t feeling fulfilled.

Afterwards, in what felt like a whirlwind, I ended up at MIT as a Fulbright Scholar and went on to co-found an e-commerce fashion startup called Stylekick. That company was eventually absorbed by Shopify, and we joined their team in the interim before being accepted into Y Combinator’s Winter ’16 class.

By the end of 2015, my co-founders and I had moved to California and our journey with Cover really began. Since then, we’ve been solely focused on building a sustainable, forward-thinking company. We currently have approximately 120 employees between two cities: San Francisco and Toronto.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

There’s no textbook that teaches you how to tackle the challenges that impact your specific business. As a co-founder, you’re in the trenches running growth testing, building product, making sales — you’re doing anything to push your business forward. But, as we hire more people to take on the bulk of those responsibilities, my role has shifted into something much different.

As CEO, my main responsibility is to build a sustainable organization and that means paying attention to both people and product. Aside from selling externally, to investors and customers, my focus has really become selling the vision to our team. I want everyone to feel like they’re an integral part of what’s happening here — for everyone to experience the special feeling of building something from scratch.

What are some of the factors that you believe led to your eventual success?

This is an odd question to answer because, in some ways, I don’t feel that I’ve achieved success yet. I’m proud of our team and what we’ve accomplished so far, but this is only the beginning.

The things that I think will lead to eventual success are having an almost maniacal focus on what customers want and continuing to pay it forward in a meaningful way. Every team has it’s highs and lows, but ultimately you just need to be resilient and constantly look for ways to create value for the customer.

It has also been important for me to remember that there’s a difference between vanity metrics and real success. Vanity metrics are things like press and valuation, but the things that really matter are revenue, retention, and how your customers talk about you.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

Lesson #1: Hire to fill out your team as soon as you have product market fit.

If your customers are paying you for the product, proactively giving you feedback, and there’s some word-of-mouth growth, you’ve probably achieved PMF. If you have, your job is quickly going to turn into hiring people that are better than you in areas like sales, product management, growth, engineering etc. despite the fact that you may have handled these functions in the past. You’ll quickly burn out and run out of bandwidth if you don’t make an effort to find these people early.

Lesson #2: Networking is usually negative ROI so don’t do it too much (if at all).

The most important thing you can do as a CEO is building something that you can execute and scale. You’ll be surprised by how vast your network will become once you’ve done this, and you will have put more time into the things that really matter.

Lesson #3: Get enough sleep and go to the gym.

This is self-explanatory, but it’s really just about staying healthy and making sure you can approach your work with a clear, sharp mind. As a startup founder, it’s easy for this simple piece of advice to be lost in the craziness of your day-to-day.

Lesson #4: Avoid vanity metrics like the plague.

Pick a metric you think will determine whether your business is successful and focus on improving it. The number of employees you have, the amount of money you’ve raised, or how fancy your office is are things that are not reflective of real success. Those things are meaningless without the context of growth in revenue, retention, word-of-mouth, and active customer feedback.

Lesson #5: You won’t improve what you don’t measure.

Have a solid analytical foundation for sales, retention, growth, and product ahead of you when you think the numbers are material. As a CEO, part of your job is predicting business outcomes slightly into the future, so having a handle on all the metrics of your business will inevitably make that job easier.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

I don’t think I’m the right person to answer this question because I’ve found it very difficult to separate my personal and business life, especially in the early stages of Cover. For me, there isn’t a clear delineation between life and work, especially since my finance is one of my co-founders.

As I mentioned earlier, my most effective technique for avoiding burnout is making sure I sleep enough and exercise regularly. That’s how I choose to recharge but every person needs to find what works for them.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There are several people who have been instrumental to my growth as a leader. The common thread between all these people is that they’re 99.9 percentile operators; they have built significant businesses to scale and have encountered every possible bump in the road. They have gone from working in their garages to having hundreds or thousands of employees. They’ve experienced success and failure, and I’ve been grateful for the ability to hear their stories.

One of my closest mentors, Danny Zhang (CTO and co-founder of Wish) has given us such a wealth of practical advice. He taught us the importance of locating problems early, solving them and swiftly moving on. Danny knows his priorities and he pursues them with a laser focus, which is something I work to emulate.

I strongly believe in building a peer group that you can leverage. I’ve come to depend greatly on the experiences (successful and otherwise) of the entrepreneurs around me.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

Right now, my goal is to become a better manager. I’ve reached a stage where I need to transition from being a scrappy founder — dipping my toes into every area whether it be growth, product or sales — towards delegating and trusting my team to execute.

On a more personal note, I’m trying to do things that inspire creativity like reading and travelling. My goals are probably not much different than anyone else’s in the sense that I strive to keep in touch with friends; stay well-read and healthy; and continue finding ways to manage a high-stress career.

What do you hope to leave as your lasting legacy?

I want to be known for creating useful, beautiful things that make people’s lives better, irrespective of the vertical. I want to be as helpful as I can to others who endeavour to build things, which is one of the reasons I’ve continued to stay active with Y Combinator.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

If I was a person of great influence who could inspire a movement, I’d want to focus my attention on building out sustainable, practical and affordable housing. I’m a big proponent of modular, manufactured housing and I think there are better ways to house and move people.

It’s possible to have people living away from major city centres while still affording them easy access to jobs and adequate shelter. I think it’s an area that is widely neglected and I’d encourage building infrastructure to accommodate technology, like autonomous vehicles, to facilitate the integration of these communities.

How can our readers follow you on social media?

https://www.linkedin.com/in/saroya/

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