Alex Douzet of Pumpkin Pet Insurance: “Accept ambiguity”

Accept ambiguity. When a new challenge arises, there is so much that’s unknown. Even in those moments, employees, customers, investors are looking to you to make decisions and as a leader, you have to be comfortable making a decision when you don’t always have all the information at your disposal. Despite that, you still need […]

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Accept ambiguity. When a new challenge arises, there is so much that’s unknown. Even in those moments, employees, customers, investors are looking to you to make decisions and as a leader, you have to be comfortable making a decision when you don’t always have all the information at your disposal. Despite that, you still need to be decisive and exude confidence.


As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times,” we had the pleasure of interviewing Alex Douzet, CEO of Pumpkin Pet Insurance.

Alex Douzet is a Serial Entrepreneur and CEO at Pumpkin Insurance Services Inc. (Pumpkin). Pumpkin is a pet insurance and wellness care provider founded to help ensure pets live their longest and healthiest lives. Prior to Pumpkin, Alex started his career in the pet care industry as CEO & Co-founder of Ollie, the next-gen direct-to-consumer natural, refrigerated human-grade pet food brand. Before Ollie, Alex was the co-founder and CEO for TheLadders, as well as Director of Online Marketing at HotJobs and the Manager of Marketing Planning and Analysis for BMG Direct.

Alex has an MBA in general management from INSEAD, an MS in direct marketing from New York University, and a BS in economy & business administration from the University of Lyon III in France. He is also a competitive Triathlete, a 7X Ironman finisher, 2015 Ironman World Championship Finisher — Kailua-Kona, a 2 X finisher of the Ironman 70.3 World Championship, and an Ironman All World Athlete (AWA).


Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I started my career in 1996, working primarily in the media and technology industry before turning to entrepreneurship in 2003 when I co-founded TheLadders.com, which became the leading online marketplace for $100K+ jobs.

In 2014, I left TheLadders, switched my focus to the animal health world, and founded Ollie, a next-gen direct-to-consumer natural, refrigerated human-grade pet food brand. I didn’t know much about animal health and good practices for dogs, but I was inspired by my rescue dog, Belle. When I adopted Belle, I fed her what I perceived as a premium pet food product, but fast forward a few months later, my dog gained 18 pounds and had digestive issues. After visiting a vet specializing in animal nutrition, who explained to me that Belle was obese and at risk of dying early, I was inspired to learn about the long-term health benefits of fresh food diets for dogs. After 18 months of work, I launched Ollie in 2016. It became very successful very quickly.

Two years ago, I got excited about another aspect of animal health: preventative medicine and veterinary care. I noticed that only 2% of pets were covered by insurance. With the rising cost of vet care and continuous innovation in the industry, I realized it was going to be more difficult for people to afford the best care unless more pets got insured.

In markets outside of the US, like the UK, the rate of insurance is as high as 25–30%. I wanted to figure out what is causing the difference and realized the need for two things: much more involvement from veterinarians as advocates for insurance and the need for a product that provides immediate value. Most pet insurance is structured only to cover accidents and illnesses, but they don’t have the right by law to cover preventative medicine like vaccines, blood tests, and check-ups.

So we came up with an idea to create a product, in addition to insurance, to address the gap. This was the premise of Pumpkin, a pet insurance and wellness care provider. Our strategy was to partner with one of the largest animal health manufacturers to have access to its strong relationships with the veterinary community, which ultimately helps raise awareness around the importance of pet insurance for their clients.

Today I am the CEO of Pumpkin, which launched in April of 2020, and just over a year into business, we’ve been named by Business Insider as “best pet insurance for comprehensive coverage.”

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

Back when I was the founder of TheLadders, the company started out so small that my two co-founders and I needed to be a “jack of all trades” of sorts. None of us were trained software engineers, so we taught ourselves coding as we went along. One day I was doing an analysis and running code on what’s called the live production database. I accidentally wrote the query the wrong way and created something called an infinite loop, which essentially took down our website for a couple of hours. The lesson I learned from that mistake was to know when it’s time to fire yourself from doing it all. After the infinite loop incident, I quickly hired a professional Chief Technology Officer.

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?

My father is definitely the person who showed me the mindset that has proven instrumental in my entrepreneurial pursuits. He taught me that success comes from one’s dedication to always learn and educate oneself. My father came from an underprivileged background raised by a single mother. He had to drop out of middle school at the age of 10 to go work, but he never let that deter him from acquiring knowledge. I admired that attribute in him and applied it to my own life. For instance, rather than run away from industries I had no knowledge of, I welcomed the opportunity to start businesses — Ollie and Pumpkin, for example — in areas where I saw the most opportunity for growth. From there, I was confident that I could learn anything I needed to know in order to build a successful business.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

Pumpkin was founded with the mission to deliver the best care possible for pets. Our work centers around the core mission to create a world that promotes a happier and healthier life for our pets. Insurance is ultimately just a mechanism that enables us to do that. Every decision we make at Pumpkin has to be in the interest of better servicing our four-legged customers.

In addition to our company’s mission for our customers, we actively seek ways to give back to organizations within our industry. Pumpkin has worked on numerous charitable initiatives where we have raised funds for veterinarians when they were hit with financial struggles during COVID, as well as fundraisers for animal shelters to both provide them with financial aid and raise awareness around the importance of pet adoption.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

During the uncertainty of COVID, I found the key was to be transparent with everybody. It was important to me to acknowledge the challenge but also highlight the opportunity for the business at a time when pet adoptions were rapidly increasing. What helped me is that I had been a CEO through prior turbulent times, namely the 2008 job crisis, when I was working at a company that relied on job postings. When COVID hit, I knew I’d be able to make it through another crisis because I’d done it before. Drawing from past experiences, I already knew what worked and what didn’t work. I was able to apply that learning to my leadership technique at Pumpkin so that I could reassure my team with confidence that we would make it through.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive

In my experience, both with myself and listening to other successful CEOs and entrepreneurs, the best leaders are the ones that don’t give up. It’s not always about having the best strategy — it’s about being persistent. If you want to be a founder or early-stage CEO where things are very shaky and unstable, it’s critical to maintain a “do not give up” attitude. In my experience, it’s the difference between success and failure. The idea of giving up cannot even enter your mind for a second.

In my personal life, I compete in Ironman races. I’ve completed seven in full, including the World Championship, and this year I’m hoping to complete my eighth Ironman. The one thing you know when you do an Ironman is that it’s a very painful, long 11–12 hour race, where you put your body through a lot of stress, and something is guaranteed to go wrong. My mentality when I’m competing is that anything is possible, but just don’t give up. I’ve always been able to finish my races which has given me the motivation to apply a similar mentality to work. Ultimately, as a founder and CEO, I know things will be challenging, but facing a challenge just means that it’s time to grow, not give up.

What would you say is the most critical role of a leader during challenging times?

A leader needs to be the one to provide reassurance and guidance to the team, despite the uncertainty; this is necessary so that employees feel confident in you as a leader and in the company.

As well, transparency is one of the best qualities a leader can have during challenging times. Employees can tell if something is off, and they can tell if you’re being honest with them. Rather than cause a situation that could result in employees losing their trust in leadership, it’s always better to just tell the situation as it is with confidence and plan on how the team will work together to overcome the problem.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

For starters, leaders need to build a team of people who are intrinsically motivated and passionate about the mission of the company. At Pumpkin, we look to recruit people who — we like to use a dog analogy for it — jump fences, or in other words, have a “roll-up-your-sleeves” mentality.

Creating a foundation for the company rooted in employees with a positive and strong work ethic allows me to tap into those traits when I need to motivate my team. This way, I know when I’m reinforcing the mission and vision of the company, despite any uncertainty and setbacks, I’m preaching to a choir of people who want to succeed for their sake and to help drive the company’s mission.

As well, we hire employees for their individual skill sets that add value to the company. It’s important to reinforce and call on your team’s strengths during times of uncertainty to help guide and remind them that you appreciate the value they provide to your company.

What is the best way to communicate difficult news to one’s team and customers?

Open and honest communication is key. Explain the reasoning behind the difficult news, what caused it, perhaps what mistakes you’ve made that led to it, and what you’re going to do to address the situation and solve it. Importantly, be willing to take questions and communicate the information more than once. Difficult news can take time for people to process and digest, but once they do, there will likely be questions, so staying open and accessible following the news is crucial.

How can a leader make plans when the future is so unpredictable?

I have a saying: a goal without a plan is just a wish. And, as part of the planning process, leaders have to anticipate that there will be things they can’t foresee. It’s not easy to build a company from the ground up. And because building a company is never a straight line, that ebb and flow in growth should be part of the plan right out of the gate.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Don’t give up.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

The biggest mistake I see are leaders who don’t act fast or decisively in challenging times. Leaders aren’t superhumans. It’s ok not to make the perfect decision all the time, but remaining paralyzed and frozen is not the way to go when you have a team relying on your guidance.

Conversely, if frequent, significant changes are occurring, it can make it seem like the ship is on fire. While leaving room for flexibility and agility is key, changing direction too frequently gives a sense of uncertainty and is extremely disruptive and confusing to a team of employees.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

A challenging economy impacts each business in different ways. Leaders have to be able to anticipate change or react quickly. It’s also important to build and maintain strong finances, so you have the capital to weather the storm if or when it comes. The best-case scenario is you can find ways to cope and grow during turbulent times. When that’s not an option, for example, airline companies weren’t able to grow when COVID began, you need to find a way to survive until the storm clears.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

  • Don’t Give Up. First and foremost, find a way to ride out the storm. Whether that’s turning to mentors, colleagues, friends, or family, find the support you need to keep moving forward.
  • Be present and accessible. When COVID began, employees who were used to working in an office and collaborating in person with colleagues were suddenly thrust into an isolated and uncertain work-from-home situation.The best thing for a leader to do in times of extreme change is to be accessible so employees feel they can trust and turn to you. It’s also important to be more present to stay in tune with the new company culture and be ready to motivate and encourage people as soon as it’s needed.
  • Reinforce goals and articulate plans that enable you to succeed. Employees turn to leaders for guidance. It’s important to create clear and achievable team goals to maintain employees’ motivation and confidence. If a goal is too vague, it can seem out of reach, and team members will be quick to lose focus. Along these lines, lay out a clear plan when possible for how teams can achieve their goals, despite an uncertain environment. In the midst of setting goals and creating plans, it’s also crucial to leave room for flexibility should things change.
  • Accept ambiguity. When a new challenge arises, there is so much that’s unknown. Even in those moments, employees, customers, investors are looking to you to make decisions and as a leader, you have to be comfortable making a decision when you don’t always have all the information at your disposal. Despite that, you still need to be decisive and exude confidence.
  • Listen. It’s important for leaders to remember to take a step back from all the chaos and just listen. What are your customers looking for? What are your employers looking for? What are your investors looking for?Listen to your partners, your stakeholders, the media, the environment, and extract the details that will help refine your thinking to focus on addressing the most immediate issues.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Life doesn’t stop teaching, therefore you shouldn’t stop learning” — Michael Josephson.

Too many people think that you’re supposed to learn when you’re young and in school, then once you graduate, you’re done learning. But learning never stops. I’ve built three companies from the ground up and led them as a CEO. Each time, the company was in a different industry. I didn’t start out in any of those industries as an expert, but I knew I could learn. As I studied the markets and industry trends, I found opportunities and ways to capitalize on those opportunities. I felt that by entering into a space with a fresh perspective, I could quickly identify how to improve a product or service in ways that people who have been in an industry for 20 years may not have otherwise noticed. Once I honed in on the problem, the success of my businesses relied on my drive to continue educating myself to keep up with industry trends and norms. I see this quote as the perfect representation of what it means to be an entrepreneur and a leader.

aaaaaaHow can our readers further follow your work?

Follow me on Linkedin and visit pumpkin.carefor more information about Pumpkin.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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