Meet 2025 Risk All Star Josh Weisberg of SterlingRisk

Josh Weisberg, chief risk
officer, managing director, RMS, SterlingRisk

It might get overlooked by the general public, but insurance brokers and brokerages face malpractice exposures just like lawyers and doctors do.

That risk was heightened when the COVID-19 pandemic forced many into remote or hybrid work roles. Remote work meant lessened oversight, which increased the possibility that a key piece of coverage or risk mitigation information might not get communicated to a brokerage client.

An oversight like that could lead to an allegation of malpractice should the client suffer what otherwise would have been a preventable loss.

To address this exposure, company leaders at SterlingRisk turned to the firm’s chief risk officer, Josh Weisberg. Weisberg and a team of attorneys and insurance experts took on the task of reimagining how educational materials on malpractice were delivered to the SterlingRisk team.

“We created buy-in from key stakeholders by following a multipronged approach,” Weisberg said. “First, we provided our service and sales staff with critical data identifying the cost behind potential errors and omissions claims for the agency and the industry as a whole.

“We offered detailed information on rising insurance premiums, higher deductible payouts, increased use of attorneys, and other expenses faced by all insurance brokerages for E&O claims in today’s insurance marketplace,” he added.

“Second, we highlighted the amount of time it takes to explore a possible errors and omissions claim and how that ties up agency resources, which draws away from an agency’s clientservice mission,” Weisberg continued.

“Because time is our most valuable commodity, showing our team how much time was expended exploring possible claim scenarios carried a major ‘buy-in’ factor.

“Finally, we provided success stories — how handling potential errors and omissions claims expeditiously backed by a ‘service centric’ approach to communications leads to stronger client partnerships,” he said.

Weisberg and team employed mixed video/live presentations to: accommodate and meaningfully engage remote service workers in E&O prevention; and keep staff current with emerging coverage products and claim trends.

“Beyond focusing on audit, adherence to best practices, and technical compliance with service checklists, Josh developed presentations anchored by guest speakers with knowledge or expertise in specific kinds of coverage or actual trial experience defending brokers in malpractice claims,” according to information provided in his Risk All Star application.

The efforts of Wiesberg and his team dramatically reduced SterlingRisk’s per incident exposure to errors and omissions claims, resulting in a more than 50% reduction in overall legal spend on malpractice claim investigation/payouts over the past five years. To achieve this success, as in many things, required persistence.

“Repetition, repetition, repetition,” Weisberg said. “We varied our approach at each meeting, bringing in different speakers to hold audience interest but never deviating from the core messages.

“Scheduling quarterly meetings and then polling participants on how the content should be rated for future discussions was critical to highlighting those topics we wanted to address. In each case, however, we made certain the top mitigation rules were always a subject of discussion,” he said. &

View All of the 2025 Risk All Stars

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