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Jay Wolfberg Named President of We Insure

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We Insure is thrilled to announce that Jay Wolfberg has been named President of We Insure. This appointment comes after an extensive search that began in July to fill this newly created position at We Insure, and after speaking with many highly qualified candidates.

“In the end, Jay was the best fit for the position and the best choice to lead us moving forward,” said Andrew McGuire, a top executive at PEAK6 InsurTech, the parent company of We Insure. “As President, he will bring with him his arsenal of skills, his abundance of industry knowledge, and an in-depth, first-hand understanding of what it takes to succeed as a We Insure agency owner.”

Wolfberg will assume this role effective September 19, 2023. 

“I’m eager to bring a new stability and perspective to the We Insure family and prioritize taking care of our three primary customers: Our agency owners, our policyholders, and our carrier partners,” Wolfberg said. “Supporting the growth of our existing agencies and expanding our footprint outside of Florida will be top priorities as well. It's clear that the We Insure business model is a successful path for both new and existing insurance professionals, and I look forward to working with the fantastic We Insure team to continue to move the company and our partners forward in profitability, growth, and protection for our policyholders.” 

Many We Insure agencies, employees, and partners are familiar with Wolfberg, who is currently the co-owner of 2 Jays Insurance Group. Located in Delray Beach, FL, “The 2 Jays” is the top-producing We Insure agency in the country. With the acceptance of the President of We Insure position, Wolfberg is stepping down from his role as co-owner of the agency and bringing his skills and knowledge to this new role.

After beginning his career as a Sales Agent/Representative at The Hartford (one of the largest and most respective insurance firms in the country), Wolfberg moved on to the role of Director of Sales for PuroClean, a leader in property emergency services that helps families and businesses overcome the devastating setbacks of property damage. In this role, Wolfberg’s leadership spearheaded the formation of a high-performing B2B sales team and the impressive expansion of PuroClean’s franchises. In the four years he was there, Wolfberg harnessed key industry relationships and maintained robust connections within the insurance sector including carrier claims departments and insurance agencies. His innovative strategies and meticulous execution helped transform PuroClean from a $10K startup to a $4M enterprise.

And then came We Insure. In 2013, Wolfberg, along with Jay Lerner, opened 2 Jays Insurance Group. As a We Insure agency owner, Wolfberg has built an impressive, $25M insurance franchise by spearheading the inception and development from a $0 book of business, achieving remarkable year-over-year growth to become three times larger than any other We Insure franchise nationwide. Wolfberg’s list of accomplishments with We Insure is extensive; below are just a few to highlight:

In 2020, doubled the franchise from $10M by navigating the challenging market dynamics of the tumultuous home insurance landscape in Florida, by adeptly strategizing to double Flood and bolster Additional Liability and Auto business segments. 

Pioneered a visionary approach to agent recruitment and training, leading a team of four Insurance Agents with no prior experience to become the industry's top performers through comprehensive Customer Service role training. 

Achieved exceptional customer retention rates, outpacing industry norms with an impressive 85-90% retention rate. 

Leveraged extensive insurance expertise to foster critical carrier relationships and negotiate favorable rates with key carriers.

Renowned for cultivating enduring relationships with fellow franchise owners, contributing to a positive, cooperative, and productive culture that promotes team cohesion and propels the organization toward sustained growth and success.

“Jay’s proven abilities to exceed sales goals, foster critical carrier relationships, provide insightful guidance on companywide initiatives, and enhance an environment of mentorship and professional growth will transfer over to support the entire We Insure organization,” McGuire said. “We are confident that in the pivotal role of President, Jay will help our agencies and carrier partners thrive while providing vital and cost-effective protection to our policyholders.” 

Wolfberg holds a Bachelor of Science in Business and Psychology from Nova Southeastern University, Fort Lauderdale, FL. He resides in West Boynton Beach, FL with his wife Juliane, two daughters, and three dogs. He prides himself on being the best chef among his friends and family, loves to host gatherings around the pool, and enjoys the outdoors.  

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