Regional Sales Director – Employee Benefits
Capstone Search Group
Listing collected from Capstone Search Group's career site. NextChapter is independent of Capstone Search Group.
Remote · Boston, MA · Posted October 27, 2026
Just laid off? Start here: a plan for the first weeks
See every open role at Capstone Search Group
More in Massachusetts job market · Financial Services & Banking · Sales jobs
Similar jobs
- Director, Incentive Compensation · Galderma Group AG/ADR · Boston, MA
- Director, Compensation · CarGurus · Boston, MA
- Defined Benefits Senior Client Manager - Virtual · Alight, Inc. / Delaware · MA
- Vice President, Total Rewards · Triumvirate Environmental · Somerville, MA
- Director, Global Compensation - Commercial · Alnylam Pharmaceuticals · Cambridge, MA
- Assistant Director, Benefits · Boston College · Chestnut Hill, MA
Where Boston, MA ranks
Where Boston, MA placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for life sciences and biotech jobs793 openings · of 41
- #1Cities with the most jobs that do not need a four-year degree in New England390 jobs · of 14
- #1Best cities for AI-skill jobs in New England21% · of 28
- #1Best cities for software and engineering jobs in New England910 openings · of 24
- #1Best all-round cities for mid-career professionals in the Northeast71 / 100 · of 26
- #1Best all-round cities for mid-career professionals in New England71 / 100 · of 11
Rankings about sales jobs
- Best cities for sales jobs #1 New York (2,774 openings)
- Best cities for sales pay after cost of living #1 Santa Clara ($175k)
- Most requested AI skills in sales jobs #1 AI tools in daily work (4.1%)
- AI tools named most often in sales jobs #1 Gong (0.93%)
- Employers with the most sales jobs #1 Charter Communications (389 roles)
How AI is used in this kind of work
AI use among compensation and benefits managers is little observed so far. Measured exposure for compensation and benefits managers: 0% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
Say which you have and which you want to build. We use it to match you to jobs like this one.
About the job
[vc_row][vc_column][vc_custom_heading text="About the Role" font_container="tag:h3|font_size:26px|text_align:left|line_height:24px" google_fonts="font_family:Lato%3A100%2C100italic%2C300%2C300italic%2Cregular%2Citalic%2C700%2C700italic%2C900%2C900italic|font_style:700%20bold%20regular%3A700%3Anormal" css=""][vc_column_text css=".vc_custom_1793122562381{margin-bottom: 50px !important;}"] This is a unique opportunity to promote business development in a new territory, playing a pivotal role in deepening broker networks, educating clients and agency contacts, and building out a new territory with a product that is not offered by others to differentiate yourself in the market. The ideal candidate will possess an entrepreneurial spirit, strong work ethic, proven success with another insurance company, and the ability to adapt to a fast-paced, growth-oriented culture. [/vc_column_text][vc_custom_heading text="Duties & Responsibilities" font_container="tag:h3|font_size:26px|text_align:left|line_height:24px" google_fonts="font_family:Lato%3A100%2C100italic%2C300%2C300italic%2Cregular%2Citalic%2C700%2C700italic%2C900%2C900italic|font_style:700%20bold%20regular%3A700%3Anormal" css=""][vc_column_text css=".vc_custom_1793122608024{margin-bottom: 50px !important;}"]
Partner with your territory’s top benefits brokers to secure group agreements as a company-paid or payroll-deducted benefit to eligible employees.
Developing key broker and consultant partnerships.
Meeting and exceeding ambitious annual targets with a dual focus on growing total premiums and membership unit volume.
Creating effective group-specific sales and marketing plans.
Traveling regularly across the territory for face-to-face meetings.
[/vc_column_text][vc_custom_heading text="Skills & Experience" font_container="tag:h3|font_size:26px|text_align:left|line_height:24px" google_fonts="font_family:Lato%3A100%2C100italic%2C300%2C300italic%2Cregular%2Citalic%2C700%2C700italic%2C900%2C900italic|font_style:700%20bold%20regular%3A700%3Anormal" css=""][vc_column_text css=".vc_custom_1793128216053{margin-bottom: 50px !important;}"]
5-7 years of Employee Benefits sales experience, preferably in voluntary benefits/worksite marketing platforms.
Currently based in Boston with an established and active network of brokers throughout the region.
Experience educating brokers about unique products.
Current A&H insurance license.
Demonstrated commitment to utilizing CRM technologies.
[/vc_column_text][vc_custom_heading text="Compensation, Benefits & Perks" font_container="tag:h3|font_size:26px|text_align:left|line_height:24px" google_fonts="font_family:Lato%3A100%2C100italic%2C300%2C300italic%2Cregular%2Citalic%2C700%2C700italic%2C900%2C900italic|font_style:700%20bold%20regular%3A700%3Anormal" css=""][vc_column_text css=".vc_custom_1793122678467{margin-bottom: 50px !important;}"] $150-200,000+ OTE + fully remote work schedule + robust benefits package [/vc_column_text][/vc_column][/vc_row]
Tagged as: business development, dental, disability, hcm, life, Sales, sales rep, voluntary benefits, wellness, worksite marketing