Regional Vice President (Boston)

The role

The Regional Vice President will drive revenue and transform how employers and employees navigate healthcare. This role involves owning a territory, building partnerships with the employee benefits broker community, and delivering tech-driven cost-containment solutions.

What you will do

• Formulate and execute a regional plan to meet or exceed revenue targets.
• Build and nurture relationships with employee benefit brokers, TPAs, and strategic partners.
• Uncover employer pain points through strategic discovery.
• Deliver platform demos and present ROI solutions to senior executives.
• Partner with Marketing, Product, Customer Success, and Sales Enablement.
• Track activities and forecast revenue using Salesforce and AI tools.
• Engage prospects at local broker gatherings, industry conferences, and client meetings.

Required qualifications

• 6+ Years in Field Sales.
• Proven track record of consistently exceeding quota.
• Outstanding communication and presentation skills.
• Willingness to travel up to 50% (local weekly meetings and 2–3 short regional trips per month).
• Must reside in or near Boston, MA.

Nice to have

• Selling directly to benefit brokers, or within HR tech, healthcare navigation, virtual care, or benefits analytics.
• Success in broker channel strategy and selling into mid-market/enterprise employers (500+ employee lives strongly preferred).

Benefits

• Stock options
• Comprehensive medical, dental, and vision plans
• Employer HSA match
• Zero-cost access to the HealthJoy navigation platform
• 401(k) with company match
• Fully company-sponsored Short-Term and Long-Term Disability coverage
• Flexible PTO
• Paid parental leave

About the company

HealthJoy is a remote-first company that uses an AI-powered Benefits Operating System to unify healthcare strategies and guide employees to affordable care.