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, Consulting & Professional Services, and Healthcare & Medical Services, with 40% remote or hybrid availability, and employers like USI Insurance Services, HUB International, and Whatnot hiring at this level now.
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The HR Benefits Analyst is responsible for the administration of health and welfare and retirement plans. The analyst is responsible for vendor management and handling employee benefits related issues. This role is currently a hybrid opportunity with Mondays and Fridays remote while Tuesday - Thursday are in office days. Occasional New Hire Benefits Orientation will require Mondays on-site half days.
What You Will Do:
- Assists with the administration of US health and welfare and retirement (defined benefit and defined contribution) plans.
- Handles employee benefits related issues including employee requests and inquiries, requests for assistance and education, issue resolution and invoicing.
- Assists new employees with benefits enrollment. Conducts new hire benefits orientation as needed.
- Ensures benefit plan vendors administer plans according to design. Monitors vendor performance and escalates issues as appropriate. Ensures issues are resolved timely. Assists in the development of vendor performance metrics, evaluation and quality improvement initiatives.
- Understands and interprets applicable benefit regulations including ERISA, PPACA, and HIPAA. Keeps current regarding legislative changes and ensure plans remain compliant. Ensures timely completion and submission of required governmental and organizational reports and filings.
- Develops and documents benefit plan processes to ensure consistent, accurate and timely processing and superior customer service. Creates, maintains, and updates documentation of process flows, administrative and standard operating procedures.
- Maintains accurate written benefit summaries, Summary Plan Descriptions and other benefit related documents.
- Contributes to content development and delivery for annual open enrollment, new hire, and life event communications as well as targeted communications throughout the year.
- Assists with annual open enrollment process including plan implementation, systems testing, and communications. Creates and reviews employee benefit communication materials. Participates in employee enrollment meetings as needed.
- Works with internal groups and vendors to support system testing, data interfaces in/out of the system, development of test plans, and the execution of plan changes and reporting. Implement and test benefit plan changes and new programs.
What You Will Need:
Education and Experience
- Bachelor’s Degree in Human Resources or a related field along with 3‒5 years of previous related experience OR
- A combination of education and experience may be applicable in lieu of a 4-year degree.
- CEBS designation preferred.
Knowledge, Skills and Abilities
- Strong technical knowledge of ERISA.
- Strong analytical, written, presentation and project management skills.
- Proficiency in Excel, Word, and Power Point required.
- Experience with Oracle Advanced Benefits is a plus.
- Obtain a working knowledge of the ABS Health, Safety, Quality and Environmental Management Systems.
Reporting Relationships:
The incumbent reports to a Manager, Director or Executive level position. This position does not have any direct reports.
The HR Benefits Analyst is responsible for the administration of health and welfare and retirement plans. The analyst is responsible for vendor management and handling employee benefits related issues. This role is currently a hybrid opportunity with Mondays and Fridays remote while Tuesday - Thursday are in office days. Occasional New Hire Benefits Orientation will require Mondays on-site half days.
What You Will Do:
- Assists with the administration of US health and welfare and retirement (defined benefit and defined contribution) plans.
- Handles employee benefits related issues including employee requests and inquiries, requests for assistance and education, issue resolution and invoicing.
- Assists new employees with benefits enrollment. Conducts new hire benefits orientation as needed.
- Ensures benefit plan vendors administer plans according to design. Monitors vendor performance and escalates issues as appropriate. Ensures issues are resolved timely. Assists in the development of vendor performance metrics, evaluation and quality improvement initiatives.
- Understands and interprets applicable benefit regulations including ERISA, PPACA, and HIPAA. Keeps current regarding legislative changes and ensure plans remain compliant. Ensures timely completion and submission of required governmental and organizational reports and filings.
- Develops and documents benefit plan processes to ensure consistent, accurate and timely processing and superior customer service. Creates, maintains, and updates documentation of process flows, administrative and standard operating procedures.
- Maintains accurate written benefit summaries, Summary Plan Descriptions and other benefit related documents.
- Contributes to content development and delivery for annual open enrollment, new hire, and life event communications as well as targeted communications throughout the year.
- Assists with annual open enrollment process including plan implementation, systems testing, and communications. Creates and reviews employee benefit communication materials. Participates in employee enrollment meetings as needed.
- Works with internal groups and vendors to support system testing, data interfaces in/out of the system, development of test plans, and the execution of plan changes and reporting. Implement and test benefit plan changes and new programs.
What You Will Need:
Education and Experience
- Bachelor’s Degree in Human Resources or a related field along with 3‒5 years of previous related experience OR
- A combination of education and experience may be applicable in lieu of a 4-year degree.
- CEBS designation preferred.
Knowledge, Skills and Abilities
- Strong technical knowledge of ERISA.
- Strong analytical, written, presentation and project management skills.
- Proficiency in Excel, Word, and Power Point required.
- Experience with Oracle Advanced Benefits is a plus.
- Obtain a working knowledge of the ABS Health, Safety, Quality and Environmental Management Systems.
Reporting Relationships:
The incumbent reports to a Manager, Director or Executive level position. This position does not have any direct reports.
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Find JobsMid Level Benefits Sales Executive Job Market
Who's Hiring
- USI Insurance Services21
- HUB International16
- Whatnot12
- Alvarez & Marsal12
- Mercer10
Top Industries Hiring
- Insurance100
- Consulting & Professional Services42
- Healthcare & Medical Services24
- Technology & Software23
- Education21
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, HUB International, and Whatnot, based on current listings on Migrate Mate as of July 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 40% of mid level benefits sales executive openings are remote or hybrid as of July 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, Consulting & Professional Services, and Healthcare & Medical Services, based on current listings on Migrate Mate as of July 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.