These Executives Love Risk

“You hardly ever see ‘entrepreneurial’ and ‘insurance’ in the same sentence,” says Stephen Sills, founder and CEO of Executive Risk. “We want people to feel the pulse of this organization.”

Executive Risk is the anti-insurance company. Yes, it is in the insurance business. But it tries not to hire people from other insurance companies. It tries not to write policies like other insurance companies. Above all, it tries not to operate at the slow pace of most insurance companies.


“You hardly ever see ‘entrepreneurial’ and ‘insurance’ in the same sentence,” says Stephen Sills, founder and CEO of Executive Risk. “We want people to feel the pulse of this organization from the first day.”

Sills, 50, is always looking for ways to infuse the company’s 575 employees with the Executive Risk ethos: The cover of a recent annual report was a metal road sign that read, “No Speed Limit”; the company’s offices feature brass bells that are rung to celebrate the sale of every new policy.

This maverick outfit, based in Simsbury, Connecticut, took shape under a blue-blooded sponsor. In 1986, Sills got a call from Aetna, which wanted to create a reinsurer that would focus on directors-and-officers (D&O) liability. The new firm would accept part of the risk associated with D&O policies, in exchange for part of the premiums. In its first year, Executive Risk wrote $80 million worth of policies. Over the next several years, it experienced steady growth — in part because other companies had pulled back from D&O coverage. Sills didn’t mind living on the edge: At the height of the savings-and-loan crisis, Executive Risk was still able to cover banks profitably.

Executive Risk emerged from under Aetna’s wing in 1994. Its main business still involves insuring directors and officers of public companies against lawsuits, as well as protecting other professionals — lawyers, accountants — against litigation arising from “errors and omissions.” This kind of insurance “scares a lot of companies,” explains Sills. “Most don’t have the stomach for seeing their clients being sued on the front page of the Wall Street Journal.”

But the Executive Risk formula has paid off. Since the company went public in 1994, its stock price has soared from $12 to a high of about $75. Annual revenues have grown as well — to more than $250 million.

The company’s early work with Aetna helped give Executive Risk a fast start. It also gave Sills strong ideas about what he didn’t want his company to become. So, from the beginning, Executive Risk set itself apart by being sharper and more responsive than its rivals. Underwriters went on “bombing missions” — quick, targeted road trips — to market the company to insurance brokerages around the country. “The big question back then was why people would buy their insurance from us,” Sills says. “Others had better brands, better ratings. From the very start, we were all about running faster, jumping higher, thinking quicker.”


Today the company doesn’t just sell differently. It also hires differently. “We hire bright, energetic people and let them loose,” Sills says. Some examples: Executive Risk’s head of sales is a nuclear engineer by training. The director of its year-2000 conversion project has a background in film studies. The employee who started its law-firm business was a deputy general counsel to the FDIC.

Of course, energy without expertise is of limited value. So, at Executive Risk, all new recruits go through an orientation program called “Building Bricks.” (It’s named after a company mantra about seeking new opportunities: “Find the loose brick.”)

After completing Building Bricks, new hires are assigned a mentor. And when they start evaluating candidates for insurance coverage, they don’t do it alone. They form a group at one of Executive Risk’s amoeba-shaped “collaborative tables” and present case files to their colleagues. “It’s a chance for junior underwriters to present a file, to talk about its merits and drawbacks in front of their colleagues,” says John Kearney, 41, chief underwriting officer.

“We’re careful to hire the right people, but we don’t let them jet off on their own trajectory,” adds Sills. “They’re part of the system, part of the network. But the system does not stifle them with a lot of bureaucracy. It just supports them.”

Energy plus expertise can generate a lot of creativity — but the right environment is equally important. That’s why there’s such a sense of play inside Executive Risk. Sills’s office decor includes the framed pizza box on which some of the company’s cofounders scribbled the notes that led to the creation of Executive Risk. Then there are the company’s funky ads (flying pigs, oven mitts) and annual reports (last year’s included a word puzzle that asked readers to spell another company slogan: “Work the Open Spot”).

“What gets us going is creativity — solving problems better than anyone else can,” says Paul Romano, 39, a vice president who leads the company’s health-care unit. “This is a community of people who get their energy from each other.”


Scott Kirsner ( writes on business and technology from Boston’s North End. You can visit Executive Risk on the Web (