High Profile: David Sterling, to Serve and Protect

For David Sterling, president and CEO of SterlingRisk Insurance, it’s always been about connecting with people and helping them.

But, Sterling’s path to building one of the largest national insurance brokers and a leading provider of risk management services and employee benefits, wasn’t always clear.

“My dream early on was to become a clinical psychologist, I loved that world,” Sterling recalls. “I was very interested in connecting with people and helping them.”

Sterling, who owns a home in Westhampton, attended the University of Wisconsin at Madison and majored in psychology. But, in a very short time, he realized he wasn’t a good fit for the field since he was “too concrete,” and psychology is a “very subjective field.”

Although Sterling was disappointed by this realization, it also helped open his eyes to an alternate career path, to possibly work in his family’s insurance business, which began life as the Central Underwriters Agency, opened in 1932 by Sterling’s grandfather and located on Park Avenue in New York City.

“I thought insurance was an interesting field,” Sterling says, as it would allow him the opportunity to explore various fields from construction and real estate to finance, and maybe one would pique his interest.

And, that’s exactly what happened. While still in Wisconsin, he switched his degree to insurance and then after moving to Long Island and finishing his degree in finance at Hofstra University, Sterling joined the family business in 1978.

“I realized the business I loved most actually was insurance, because it enabled me to connect with many different people in various businesses,” he says, adding, “You’re protecting people by providing them with coverage they can afford and still help them. … It’s what I always wanted.”

Fast-forward to 42 years later, and Sterling has a “career I was made for and didn’t even know it.”

Today, SterlingRisk Insurance has eight locations from New York to Florida and provides clients with business insurance, consulting and personal insurance in a variety of industries from architecture and aviation to restaurants and retail.

But, more than anything, Sterling says that among his most prominent accomplishments is assembling a team of professionals who have helped build the now 90-year-old company.

“You can’t get the type of growth we’ve enjoyed without the right people,” he says.

Sterling also points to the company’s development of “some of the most creative insurance products in the industry in the past 40 years.”

He says that since 2009, the company has tripled in growth, with most of that being organic as opposed to acquisitions.

“Our growth is across the board and not attributed to any one area, except for maybe real estate, which has grown well in New York over the years.”

He credits his wife, Mona, for some of that growth.

“My wife is a real estate developer. … I met her in 1996 and much of the company’s spectacular growth started then,” he says. “A great deal of what I’ve been able to accomplish has been because of her.”

He adds that the company helped to pioneer selling the first online insurance policies, back in the days when Western Union was still using its Telex system, predating the internet.

“We sold some of the very first insurance policies online,” he recalls.

Asked how the ongoing pandemic has affected the company, Sterling says he’s remained flexible since the beginning.

“I was following the events in China from the start and made the early decision to be flexible and let my team work the way they’re most comfortable and felt safest.”

He says the pandemic had some unintended consequences, such as “exposing people to a lifestyle few knew existed,” allowing people to get things done at home while still working and remaining productive.

“I’m not making any demands on employees to come back to the office … people can use a hybrid model, couple days in office and then at home,” Sterling explains.

“In many ways, I’m not the leader,” he says. I’m following my employees.”

Sterling’s philanthropic life is centered mainly around donating and volunteering with AIPAC (American Israeli Public Affairs Committee) and the UJA Federation.

He explains that he supports the organizations to help combat the ongoing societal problem of antisemitism, or persecution of Jews.

“Through a combination of my own personal feelings, as well as history and facts, Jews continue to be one of the most persecuted groups in the world throughout history,” he says. “It just feels right to me … to help Jews who need it and also to build bridges between the Jewish community and other racial, religious and ethnic groups, as well as to help strengthen the U.S.-Israeli alliance.

Sterling also serves on numerous charitable boards and gives to a wide range of organizations, such as Habitat for Humanity, which builds housing for the homeless.

“Because these issues affect all of us,” he adds.

This story first appeared in The Villager.