Mid Level Benefits Sales Executive Jobs
Mid level benefits sales executive jobs go to professionals ready to own client portfolios, lead renewal cycles, and close group benefits deals with limited day-to-day oversight. Openings run across Insurance and Law & Legal Services, with 17% remote or hybrid availability, and employers like USI Insurance Services, Aon, and Symetra hiring at this level now.
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Holland & Knight is seeking a talented executive compensation and benefits associate with a minimum of 3+ years of experience to join the Firm’s Executive Compensation & Benefits Practice in its Philadelphia, Dallas, NY, Charlotte, Chicago or Nashville office. Our ideal candidate will have 3+ years of experience advising on executive compensation and employee benefits matters with a particular emphasis on such matters within the context of mergers and acquisitions. Experience with equity compensation for corporations and partnerships and IRC Sections 280G and 409A is also required. Qualified candidates will have excellent academic credentials and superior writing, oral communication and analytical skills.
EOE. M/F/D/V. In accordance with the New York City Human Rights Law the pay range for this position in New York City is $260,000 - $360,000. This range is specific to this location and may not be applicable to other locations. An individual's actual compensation will depend on the individual's qualifications and experience.
- 3+ years of experience.
- JD from an ABA Accredited Law School.
- Must be licensed or ready to become licensed in the jurisdiction of hiring office.
- This candidate must reside in the designated jurisdiction at or prior to the time of hire. We believe that there is significant value in working together in person and will expect the candidate to work in the office at least three business days per week.
This position may be filled in any Holland & Knight U.S office. In accordance with Pay Transparency Laws, the pay range for this position in Colorado, California, District of Columbia, Illinois, Massachusetts, New York, Virginia and Washington is $260,000 - $360,000/yr. This range is specific to these locations and may not be applicable to other locations. An individual's actual compensation will depend on the individual's qualifications and experience.
Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found here under "Well Being Program and Benefits".
Holland & Knight is seeking a talented executive compensation and benefits associate with a minimum of 3+ years of experience to join the Firm’s Executive Compensation & Benefits Practice in its Philadelphia, Dallas, NY, Charlotte, Chicago or Nashville office. Our ideal candidate will have 3+ years of experience advising on executive compensation and employee benefits matters with a particular emphasis on such matters within the context of mergers and acquisitions. Experience with equity compensation for corporations and partnerships and IRC Sections 280G and 409A is also required. Qualified candidates will have excellent academic credentials and superior writing, oral communication and analytical skills.
EOE. M/F/D/V. In accordance with the New York City Human Rights Law the pay range for this position in New York City is $260,000 - $360,000. This range is specific to this location and may not be applicable to other locations. An individual's actual compensation will depend on the individual's qualifications and experience.
- 3+ years of experience.
- JD from an ABA Accredited Law School.
- Must be licensed or ready to become licensed in the jurisdiction of hiring office.
- This candidate must reside in the designated jurisdiction at or prior to the time of hire. We believe that there is significant value in working together in person and will expect the candidate to work in the office at least three business days per week.
This position may be filled in any Holland & Knight U.S office. In accordance with Pay Transparency Laws, the pay range for this position in Colorado, California, District of Columbia, Illinois, Massachusetts, New York, Virginia and Washington is $260,000 - $360,000/yr. This range is specific to these locations and may not be applicable to other locations. An individual's actual compensation will depend on the individual's qualifications and experience.
Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found here under "Well Being Program and Benefits".
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- Law & Legal Services
Mid Level Benefits Sales Executive Jobs: Frequently Asked Questions
How do I get a mid level benefits sales executive job?
Position your experience around measurable outcomes: revenue generated, accounts retained, and benefits packages you have sold or managed end to end. Hiring managers at this level want candidates who can demonstrate client ownership and consultative selling ability, not just administrative support. Highlight proficiency with voluntary and employer-sponsored benefits, and make sure your resume reflects the full scope of decisions you have made independently.
Which companies hire mid level benefits sales executives?
Companies hiring mid level benefits sales executives right now include USI Insurance Services, Aon, and Symetra, based on current listings on Migrate Mate as of September 2026. Carriers, regional brokerages, third-party administrators, and large insurance agencies tend to hire most actively at this level, particularly those expanding their group benefits or voluntary worksite offerings.
Are there remote mid level benefits sales executive jobs?
Yes, remote and hybrid options are common in benefits sales at the mid level. About 17% of mid level benefits sales executive openings are remote or hybrid as of September 2026, reflecting how much of the benefits sales process, including quoting, enrollment support, and client check-ins, can be handled digitally. Territory-based roles may require some in-person client presence even when listed as hybrid.
How do I move up to a mid level benefits sales executive role?
The path from entry level to mid level in benefits sales is built on demonstrated ownership. Early-career professionals grow into this tier by managing their own book of business, learning to navigate open enrollment cycles independently, and developing fluency in plan design across medical, dental, vision, and ancillary lines. Earning credentials such as a Group Benefits Associate designation and showing consistent retention and growth metrics accelerates the transition.
Which industries hire the most mid level benefits sales executives?
Mid Level benefits sales executive roles concentrate in Insurance and Law & Legal Services, based on current listings on Migrate Mate as of September 2026. These sectors drive hiring at the mid level because they serve large employer groups with complex, ongoing benefits needs that require experienced sales professionals who can manage relationships and renewals without heavy supervision.