Steve Dresner Identifies and Spends on the Things That Matter

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Although Steve Dresner is a respected insurance executive with nearly forty years in the industry, he came upon the industry by accident. The year was 1984, and a young Clark University graduate from Massachusetts did what most new professionals did in that era: he answered a want ad in the local newspaper.

Dresner didn’t know exactly what he was getting into when he started an entry-level position at reinsurance agency Gen Re, but over the years, he’s traveled the world, learned about the trade, made lifelong friends, and found a home in his career.

Now, as president of Everspan Group, Dresner leverages his unmatched expertise to build a strong internal team, develop new business opportunities, and keep the company executives on pace with their strategic goals.

Profile spoke with Dresner about how the right leadership approach will take Everspan to new heights.

You’ve spent an entire career in insurance. What made the move to Everspan right for you?

Everspan was started in 2020 by our parent company, Ambac Financial Group, and I had the chance to be the second employee as the chief underwriting and reinsurance officer. It was a startup environment, and we had the opportunity to assemble a team and build culture from the ground up. It was really exciting at this stage in my career.

The timing was interesting. It was July 2020? 

Right in the heart of COVID.

How did that change things?

We built the company virtually. We had to hire employees without meeting them in person and still foster a sense of collaboration. There were challenges, but it also meant we could reach a customer base that we never would have been able to reach in a traditional setting.

Can you explain? 

I’ve spent my career meeting people face-to-face. You set up meetings, get on a plane, go into an office, and make your pitch to prospective customers. That takes time and money. We didn’t have the time or ability to travel, so we had to be efficient. We set up multiple video calls per day and chose to be selective in building our book of business.

What sets Everspan apart?

We bring oversight controls and a technical acumen that some of our peers don’t. We’re very responsive and are transparent with our partners, which we believe will foster strategic growth long-term.

You were elevated to president in 2022. What kinds of things are you focused on in that role?

We received our AM Best rating in 2021, and that meant we could start soliciting business. Since then, we’ve acquired insurance carriers and gotten our licenses and the ability to work in all fifty states. Now we’re focused on taking what started as a small company and maturing it.

You and the others at Everspan have accomplished a lot in a short amount of time. What are you most proud of?

We’ve gone from starting in 2020 to featuring a broad product line of twenty-two programs and over $273 million in gross premium at the end of 2023. At the same time, we’ve hired staff and implemented risk management controls. Bottom line, we feel like we’ve grown the right way!

What’s top of mind for you right now?

We want to become more efficient as we grow and achieve economies of scale. Those are big goals for us.

Tell me about the team you’ve been building. What’s it like?

The number one most important thing is to bring in a group of diverse people and build a culture. We have most of our staff in New York City and a complement of remote workers across the US. Diverse teams help companies grow.

Is it challenging to lead a hybrid team?

It can be, but we really focus on bringing the team as often as possible. We unite everyone once a quarter in New York so we can go over results and grow as a team. That’s money well spent.

What are some parts of the Everspan culture?

Two big things for me are respect and transparency. Some companies want to act like problems don’t exist, but I’m the opposite. I want to know what’s happening. When we uncover problems here, the entrepreneurial spirit we were founded with kicks in, and everyone wants to improve the situation.

How have you crafted your approach to leadership over the years?

Listening is key. Everyone wants to speak all the time, but you learn so much when you simply take the time to actually listen. I talked about diversity earlier. We’ve worked hard to onboard a lot of smart people. There are great employees here who know more about certain aspects of the business than I do. It would be foolish of me not to listen to them.

How do you find opportunities to support others and give back?

Most recently, I’ve become involved supporting the work of the Association of Professional Insurance Women. I encourage people to get involved with groups like that. This has been a male-dominated industry, and I want to find ways to improve opportunities for everyone.

What’s next?

At this point, it’s building and leaving a legacy. We want to leave something better than it was when we came, and we want to create something that people want to be a part of.

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