Five Questions With: Gary Heaslip

Gary Heaslip is president for Cross Insurance Inc. – Rhode Island, located at 376 Newport Ave. in East Providence. Cross Insurance is an independent agency based in Bangor, Maine.

In his position, Heaslip is responsible for all the agency’s operations throughout Rhode Island. He previously served as an executive at Cross Insurance, overseeing the agency’s growth through new production and the acquisition of agencies and producers in Rhode Island. Prior to joining Cross Insurance, he served as vice president/sales manager for Cross subsidiary TGA Cross in Wakefield, Mass.

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Founded in 1954, Cross Insurance has about 800 employees in more than 35 offices, serving 100,000 customers throughout New England.

The family-owned and -operated Cross Insurance, a subsidiary of Cross Financial Corp., provides insurance and financial products, including personal and commercial insurance lines, employee benefits, surety bonds, risk-management services, and specialized products focused on higher education and high net worth needs.

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PBN: How did you become president of Cross Insurance – Rhode Island?

HEASLIP: I opened Cross RI back in 2014. Cross was looking to expand their footprint in Rhode Island, which has been dominant in Maine and New Hampshire, and has grown exponentially in Massachusetts.

As the preferred broker for the majority of the New England sports teams – i.e., [New England] Patriots, [Boston] Red Sox, [Boston] Bruins – we have a significant platform to build upon. The Connecticut marketplace is now burgeoning as well.

PBN: Which lines of insurance does the company offer and which ones tend to be more lucrative?

HEASLIP: We are a full-service agency offering all lines of coverage – business, personal, benefits, etc. We are intensely client-focused, with a passion to utilize our intellectual capital to ensure the optimum, cost-effective outcome to every transaction.

PBN: What would you say has been your top career accomplishment?

HEASLIP: Looking back, the top accomplishment – hands down – is having achieved the top score in the country four times in various insurance designation curriculums. I’m the only person in New England to achieve this recognition.

PBN: What is the biggest challenge facing independent insurance agencies?

HEASLIP: We are at the mercy of a marketplace, which is often controlled by influences such as hurricanes, earthquakes, etc. The other challenge is to completely understand the exposures our clients face in a rapidly changing world with the advent of social media and other exposures.

PBN: What employment issues does the industry face?

HEASLIP: Sourcing talent. We have corporately overall experienced/achieved success in hiring outside of the industry. Looking for individuals with the requisite skill, passion and intensity that will translate to providing an environment for the individual to self-actualize in a challenging, dynamic workplace.

Scott Blake is a PBN staff writer. Email him at Blake@PBN.com.