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Jesse O'Boyle

Helping you navigate the rapidly evolving insurance landscape.

As Employee Benefits Consultant, Jesse works closely with employers to strategize for future benefits plans, proactively maintain compliance and implement new technology for the administration of their benefit plans. He takes the time to first listen to a client’s needs, learn their priorities and provide long-term solutions to meet their goals. With a strong focus on transparency and accountability, Jesse is passionate about building strong partnerships to provide a positive experience for his clients and their employees.


  • More than 16 years of experience in the insurance industry
  • More than a decade of experience assisting businesses with cost saving solutions and educational resources
  • Strong background in providing benefits strategies to employers of all sizes

Insurance products offered by Johnson Insurance Services, LLC, a Johnson Financial Group Company. Not FDIC insured, not a deposit, not insured by any federal government agency, not bank guaranteed, may lose value.

Ask Me About

  • Strategic Employee Benefits Consulting
  • Health Insurance Funding
  • Benefit Compliance and Regulatory Support
  • Employee Health and Wellbeing

Community Involvement

  • Formerly served as an Employer Contact for United Way, spreading the mission of United Way through employer groups across two counties in Wisconsin

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