Cleary Insurance: Supportive, Family Atmosphere That Puts Employees and Clients First

By Jahna Jacobson

Cleary Insurance Inc. is an insurance company with a great team, a winning atmosphere, and a “family vibe.”

That’s according to employees who nominated Cleary Insurance Inc., Insurance Journal’s Best Agency to Work For Gold Award winner for the East region.

“It is the best place to work because it fosters both professional growth and personal fulfillment,” one employee said. “A strong team means collaboration, support, and shared successes. Employees lift each other up and celebrate wins together. A winning atmosphere drives motivation and pride, encouraging everyone to strive for excellence while feeling valued.”

The family atmosphere and positive, supportive company culture developed through years of intentional hard work and listening to the needs of employees.

“It gives me an incredible sense of pride to know that our staff nominated Cleary Insurance for this award,” said agency owner and President Bill Cleary.

When COVID hit, he worried that moving the team to remote work would erode that culture.

“Fortunately, we have a mature and selfless group of people here, and they have continued to keep that culture alive and thriving,” Cleary said. “I think they nominated us because they enjoy working with each other. Working alongside people you respect and enjoy is what makes this a great place to work.”

Employees said they appreciate the absence of micro-management and a feeling of autonomy.

The agency gives everyone the authority to make decisions on their own, to “do the right thing” without needing to consult a manual or a superior, Cleary said. “I believe our structure is a truly defining characteristic: we have a very flat organization, with virtually no middle management.”

No matter what position a person holds, they are always willing to pitch in, said another employee. “They have created a true team environment where everyone is respected.”

Cleary’s employees also said there is a genuine emphasis on work-life balance in the family-run agency.

“One of our co-workers had heart surgery and took extended leave from work,” one employee said. “She has commented on how well she was helped with disability benefits and has been kept on part-time because she is not yet able to return full-time.”

Another employee found ample support through a recent cancer diagnosis.

“My job was a concern for me, not knowing what would happen,” they said. “Well, as it turned out, there was absolutely nothing to worry about. Bill Cleary made sure I felt comfortable, not pressured to get back to work, always checking on my progress without pushing…It makes working on my recovery time less stressful, and I knew he and everyone at Cleary had my back.”

When it comes to compensation, employees note cost-of-living increases, fair pay based on merit and accomplishment, bonuses, and exceptional profit-sharing and retirement programs.

And no one works harder than Cleary and Vice President and Chief Operations Officer John Bernardin, several employees commented.

“Both of them keep an open-door policy, and I can confidently say everyone loves to go to work at Cleary,” one said. “I have never worked at an agency with such a healthy working environment that also strives to continue to do better for employees and clients.”

The growing agency added eight people in the last year, an employee said in their nomination, adding, “Our new employees recommend our company to their friends.”

Finding new team members through current employees works well for the agency, Cleary said.

“The employees feel invested in our culture, respect each other, and thus they are usually the source of where we find our new employees,” he said. “They work hard to find new staff that will fit in and appreciate the culture they have established.”

“Don’t hire by technical skill sets,” he added. “Hire good people, then get out of their way and let them do their thing!”