Talent Acquisition June 09, 2022
Talent Acquisition June 09, 2022

10 Questions with Jon Cooper, CEO of Overalls

As part of our “10 Questions with Redesign Health CEOs” series, we welcome Jon Cooper, Co-Founder, and CEO of Overalls, a modern benefits company that combines concierge-like services with tailored financial protection products in a delightful experience designed to save time, celebrate milestones, and protect the things we care about. Learn more about Overalls and other Redesign Health Operating Companies here.

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 Overalls is a modern benefits company that combines concierge-like services with tailored financial protection products in a delightful experience designed to save time, celebrate milestones, and protect the things we care about. Learn more about Overalls and other Redesign Health Operating Companies here.

Overalls offers head-to-toe coverage for life’s ups and downs. We’re on a mission to make insurance engaging, personalized, dynamic, and accessible by offering concierge-like services with tailored financial protection products. Overall’s fresh approach to employee benefits allows users to reclaim the time, joy, and money people lose to all of life’s hassles.

  • 1. What does redesigning health mean to you?

    Redesigning health means tackling an incredibly multifaceted issue at a systemic level. Everything’s connected — when it’s hard for kids to get a good education and hard for people to be financially resilient, that makes it difficult for people to be healthy. That’s the core of what I and others from Redesign Health enjoy focusing on — recognizing the unique challenges of those separate components and building companies that target and solve different pieces of the healthcare puzzle.

    Redesign Health has created an innovation model that caters to an underserved market of founders — passionate and skilled entrepreneurs who aren’t at a life stage compatible with living off ramen noodles and bootstrapping a business in their garage, or investing a few million extra dollars of personal capital to start a new business. Not to mention, all the not-so-little things that take up time and resources but don’t truly advance the business (such as forming a corporation, opening a bank account, and having capital to start with) are all taken care of.

  • 2. What role does curiosity play in innovation?

    If you examine how systems change, it’s mainly through one of two ways — innovation or legislation. Of those two, innovation is the best way to change a system, in large part because it’s fueled by curiosity. You see the impact of curiosity everywhere, how it can dramatically change the way we do everything: think about the advent of the internet or the microchip. Curiosity led to these breakthroughs that resulted in a cavalcade of systemic change.

  • 3. What is the most crucial decision you made in the first 100 days of launching Overalls?

    Many businesses face the same challenge that we faced: we’ve identified an idea that’s really good on paper and addresses a largely underserved market. It then becomes a question of taking that opportunity and establishing the perfect product-market fit.

    Staying flexible and being willing to incorporate customer feedback early on is so important — if you don’t do that, everything else is more complicated downstream. Tinkering with our original idea catalyzed a real breakthrough. Early on, the general reaction from companies was something along the lines of, “That’s a good idea, talk to me in six months,” but by the time we really honed in on what mattered to our target market, the reaction changed to, “Oh my gosh, I’ve never seen anything like this! How do I sign up?"

  • 4. What’s the most unexpected lesson you’ve learned through your journey as a founder?

    I under-appreciated the power of a well-crafted brand. This is something I learned specifically from Laurie Ann Goldman (the former CEO of Spanx and CEO of Avon), who was an advisor to Redesign Health and now sits on my board. Our website utilizes an eye-catching headline that incorporates a hashtag: $#it happens. One of our first clients came to us out of the blue — they said, “we saw your tag line and website, and it resonated with us.” I’ve come to learn that it’s as much what you’re saying as how you’re saying it.

  • 5. What’s the most important feedback you’ve gotten from a customer? What role did it play in shaping your business?

    We came into being at a very unique moment in time: while the insurance market is quite saturated, COVID-19 and the Great Resignation have introduced a renewed urgency regarding solving universal problems. Overalls has very clear messaging regarding the concrete ways we can help people save time, money, and celebrate life in a significant way.

    When we initially went to market, we were more vaguely positioned to offer better voluntary benefits — and we weren’t getting as enthusiastic of a response from employees and employers as we had expected. Voluntary benefits can’t bring people greater peace of mind if no one really understands them. So we repositioned everything to focus on three core products with clear offerings: Hassle Helper, Pocketbook Protector, and Mighty Moments.

    We reframed Pocket Protector, for example, to clarify that it can save you money today and in the future. This voluntary benefit began to resonate with people when we clearly stated that, essentially, we save you money through offering better insurance options, and then take a portion of the money you’ve saved and put it in a rainy day fund.

  • 6. What’s the key to building trust with your employees and customers?

    Your company can be composed of 99% of the right people, but one wrong person can set fire to the whole thing. Transparency is key to the hiring process. When you combine transparency and trust with the right people, those people tend to work hard. They feel valued and that they’re being treated as real human beings.

    Something we do that builds trust and strengthens our team environment is a company-wide show-and-tell twice a month. Everyone across the company has the opportunity to show everyone else what they’ve been working on and get a response from individuals in each department. This creates a unique window into the disparate parts of our operational processes, and creates a wider appreciation for the company as a whole.

  • 7. What’s your top expectation from your team?

    You don’t have to create a pressure cooker, investment banking type culture in order to achieve high output. It’s more of a question of bringing in great people, who tend to have very high expectations of themselves, and helping them understand what the big picture is. Leading with empathy is really important when it comes to bringing out the best in your employees.

  • 8. What’s the first thing you do when you get out of bed in the morning?

    My morning routine consists of a double espresso, a cold-ish shower, and ten minutes of direct sunlight. I know it sounds nuts, but it actually makes a huge difference in my energy level and mood, and there is an increasing amount of scientific evidence supporting the benefits of sunlight and cold exposure. Not sure about the double espresso though…

  • 9. What brings you the most joy — inside and outside of work?

    I love spending time with my family (particularly when the kids are behaving). Also, my Mom is French, so the French culture is important to me. I’d love to teach my family French and live in France for a year.

  • 10. What’s a fact others may not know about you?

    I’m trilingual! I speak French, Spanish, and English.

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Jon Cooper Co-Founder & CEO

Jon Cooper is Co-founder & CEO of Overalls, a tech-enabled benefits company that combines concierge-like services with personalized financial protection to help people save time, money and stress. A repeat insurtech entrepreneur, Jon was previously founder and CEO of Life.io, a pioneer insurtech that successfully recast digital customer engagement for life insurance. He led the business from inception to private equity and strategic acquisition. Prior to Life.io, Jon held various strategic roles in the insurance industry, from Chief of Staff to Strategy and Operations at TriZetto, Oliver Wyman, CodeRyte and Wellcare.

Jon has an MBA from the Wharton School where he received the Wharton Venture Fellowship and was double-awarded the Snider Seed Grant, which enables students to take innovative business ideas from ideation to implementation. He has a Bachelor’s Degree from the University of Pennsylvania.