Regional VP, Mid‑Market Health Benefits (Remote)

HealthJoy; Boston (MA); Remote; USD 275,000 - 300,000; Full time

Benefits offered by this job

Medical, Dental and vision insurance

Stock options for eligible roles

Paid parental leave

Disability coverage (short and long)

Flexible PTO

Job summary

HealthJoy is seeking a Regional Vice President for the Mid Market segment (100–3K employees) to build a territory, drive sales cycles, and close business with employee benefits brokers. This remote-first role resides near Boston, MA with up to 50% travel to broker and employer meetings.

The position emphasizes hunter mindset, broker partnerships, and executive-level communication. Target total compensation ranges reflect base plus commissions.

Qualifications

• Minimum of 6 years of related field sales experience; ideal to have broker partner experience.
• Proven success in broker channel sales with track record of acquiring partnerships.
• Experience selling to mid-market employers (100-3K employees) is highly preferred.
• Assertive self-starter with strong relationship management & negotiation skills.
• Proven track record of achieving sales and revenue goals.
• Strong interpersonal communication and presentation skills with senior management.
• Ability to travel up to 50% of the time.

Responsibilities

• Exhibit tenacity and proactive mindset to drive broker and employer meetings; execute decisive actions to drive results.
• Demonstrate strong discovery skills to uncover employer and broker needs and priorities.
• Present with executive presence to C-suite executives; tailor communications accordingly.
• Travel up to 50% for local and out-of-town meetings to advance deals.
• Meet or exceed assigned sales objectives via broker prospecting, lead generation, proposals, and forecasting.
• Collaborate cross-functionally with Sales, Marketing, Customer Success, Product and Enablement.

Skills

Broker sales

Healthcare navigation

Employee benefits tech

Virtual care services

Healthcare data analytics

Job description

HealthJoy is seeking a Regional Vice President for the Mid Market segment (100–3K employees) to build a territory, drive sales cycles, and close business with employee benefits brokers. This remote-first role resides near Boston, MA with up to 50% travel to broker and employer meetings.

The position emphasizes hunter mindset, broker partnerships, and executive-level communication. Target total compensation ranges reflect base plus commissions.