Trupanion CEO Margi Tooth Leads the Pack

Growing up on a farm in the United Kingdom, Margi Tooth dreamed of channeling her love for animals into a career as a veterinarian. Although she took a different path—working in market research and business development before moving into the insurance sector—she still ended up with a job that helps animals. Tooth is the CEO of Trupanion, the Seattle-based pet insurance provider, where she has worked for the past 13 years; she stepped into her current role in August 2024.

“I saw a company breaking the mold,” Tooth says of her first impressions of Trupanion, “building true, high-quality pet medical insurance in a space with enormous growth potential. Perhaps even more important, I saw a way to help end economic euthanasia, the tragic reality of losing a pet simply because the cost of care is out of reach.”

With two dogs, a tortoise, and three sons at home, Tooth is busy, but she makes time to mentor her team, continue building the brand—the company insures more than a million pets and has more than $1 billion in yearly revenue—and take some much-needed time for herself.

“My strategy is to live up to the promise we make to our members and our team every single day: to do what we say we will do, and to do it with conviction,” Tooth notes. “I’m passionate about fostering an environment where people can truly thrive through trust and collaboration, allowing us to find the best possible solutions to the challenges pet parents and veterinarians face.”

Interview has been edited for length and clarity.

Biggest inspiration

I’ve been fortunate to have several incredible mentors. Aside from my husband—without whom none of this would be possible—my biggest inspiration is easily Darryl Rawlings. As the founder of Trupanion, Darryl inspired me in ways no one ever had before. He taught me to allow myself to think differently, to have confidence in my instincts, and to basically be me. It’s simple advice, but the best I’ve had.

Lessons learned

I’ve learned to stay open, to be a lifelong learner, and to accept that no one has all the answers. It is okay to fail, and it is more than okay to ask for help. Early on, I viewed asking for support as a weakness; I’ve since learned it’s a vital strength.

Perhaps the biggest lesson is understanding the power of a high-performing team. I’ve always been a people person—empathetic and a firm believer in human potential. The more tenured I become, the more I see how critical it is to create a unified team. When you trust your gut and go the extra mile to support your people, the business thrives.

Leadership

Good leaders are open-minded, focused listeners, and maintain a consistent balance between heart and head. They must also be constant learners. I truly believe everyone is a teacher, and a leader should always be open to the lessons those around them have to offer.

Advancement advice

First, ask yourself why you want to advance and what is driving that desire. I didn’t meticulously plan a pathway to the CEO role, and I think that’s true for many leaders. You have to work hard, raise your hand for the hard opportunities, take risks, and communicate clearly.

Navigating workplace barriers

I’ve always pushed myself outside my comfort zone, which has often meant being the only woman at the table. When you’re in that position, don’t let the optics distract you from your purpose. Own your seat. No one puts you in a high-level role as a favor; they do it because they believe in your value.

I’ve faced moments when people were discouraging or patronizing regarding my role as a leader or a hardworking mum. When faced with judgment, stick to what you know and let your passion carry you through. Don’t let the noise crowd your mind. I also strongly encourage finding a mentor you trust to talk through these challenges; you don’t have to find all the answers alone, and there is great power in vulnerability.

Overcoming negative self-talk

You don’t suddenly acquire all the answers the moment you become CEO. One benefit of seniority, however, is that you get a lot of practice overcoming that doubt.

I rely on a small, trusted circle to help me navigate those moments. It’s important to get a second voice in the conversation when you sense doubt creeping in—it provides a necessary reality check. To overcome negative self-talk, I start with the facts rather than the “fiction” of my own head. I look at what I know to be true, stress-test the options, and weigh the pros and cons. Remember: you are where you are because you earned it.

Networking

I’ve never been a fan of networking for the sake of it; I’m a firm believer in building genuine partnerships. My approach has always been to connect with people I can learn from—and, I think this is key, where I can offer something of value in return. Connections for me need to be mutual. If I meet like-minded individuals, that’s a bonus—and it sometimes leads to something much larger than a simple connection.

Do differently

I wish I had had the wisdom and confidence to trust my instincts earlier. They rarely let you down. Early on, I let others deter my decisions because I believed in them more than I believed in myself. That confidence comes with experience, but a lack of it can be a real detractor.

On a personal note, like any working parent, I have “mum guilt” about time spent away from my family. I frequently wish I could carve out more time for them. My husband and children are my greatest supporters; I categorically would not be in this position today without them as my motivation and my drive.

Day off

Unsurprisingly, I’m with my boys—my husband and my three sons. We love traveling together, going for family walks, watching soccer (or football, as I still call it!), and visiting family and friends back in the UK. I’m also a keen runner, and I like to balance that out with a glass of wine or a cheeky cocktail.