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USA remote

Regional Vice President (Boston)

HealthJoyBoston, MAPosted 26 Sept 2026

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About this role

*HealthJoy is a Remote-first company, but the person in this position must reside in or near Boston, MA - with travel up to 50% Come for the mission. Stay for the innovation. Healthcare is broken, confusing, and costly—and HealthJoy is fixing it. We’re on a mission to remove the complexity from staying healthy and well. Through our AI-powered Benefits Operating System, we unify messy healthcare strategies into a seamless digital experience that guides employees to high-quality, affordable care.

The result? Happier, healthier teams and a massive reduction in healthcare costs for employers. We are reshaping an industry in desperate need of innovation, and this role sits directly at the engine of our growth. As the front line of our mission, you aren't just selling software—you are empowering brokers and employers to fundamentally transform how people access healthcare. If you're looking to take true ownership of a territory, drive high-visibility commercial impact, and build a massive success story, this is where you do it.

Your impact. Healthcare is complex, confusing, and costly—and HealthJoy is changing that. As Regional Vice President (RVP), you’ll be at the center of our growth story, driving revenue and transforming how employers and employees navigate healthcare. This isn’t just a sales role; it’s an opportunity to own a territory, build high-value partnerships across the employee benefits broker community, and deliver tech-driven cost-containment solutions that make a measurable impact.

If you thrive in a fast-paced environment with high autonomy, uncapped earning potential, and a mission you can get behind, HealthJoy is where you can build something meaningful. Our sales team members possess the following key behaviors: Mission-Driven & Buyer-Centric: You put employer and broker needs at the heart of every interaction, solving real healthcare pain points rather than just pitching features. Relentless Ownership: You love the chase, take initiative at every stage of the sales journey, and take full accountability for driving deals across the finish line.

Strategic Relationship Builders: You focus on long-term trust and high-quality partner relationships over quick, transactional wins. Agile & Coachable: You embrace continuous learning, welcome feedback, and adapt quickly to market opportunities and new product strategies. Collaborative Trailblazers: You leverage modern tools (including AI), test new sales strategies, and partner seamlessly across marketing, product, and enablement to elevate the entire team.

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Your will: Execute Territory Growth Strategy: Formulate and execute a regional plan to consistently meet or exceed monthly, quarterly, and annual revenue targets. Cultivate Broker Alliances: Build and nurture deep, trusted relationships with employee benefit brokers, TPAs, and strategic partners across your assigned region. Lead Discovery & C-Suite Pitches: Uncover employer pain points through strategic discovery, deliver impactful platform demos, and present tailored ROI solutions to senior executives.

Orchestrate Cross-Functional Deals: Partner with Marketing, Product, Customer Success, and Sales Enablement to align go-to-market strategies and maximize win rates. Maintain Pipeline Discipline: Utilize Salesforce and modern AI tools to track activities, maintain clean pipeline data, and accurately forecast revenue. Represent HealthJoy in the Field: Engage prospects at local broker gatherings, industry conferences, and client meetings, traveling up to 50% within your territory.

Your experience. 6+ Years in Field Sales: Proven track record of consistently exceeding quota—ideally selling directly to benefit brokers, or within HR tech, healthcare navigation, virtual care, or benefits analytics. Channel & Employer Expertise: Demonstrated success in broker channel strategy and selling into mid-market/enterprise employers (500+ employee lives strongly preferred). Executive Presence: Outstanding communication and presentation skills with a natural ability to command C-suite conversations and articulate complex cost-containment value.

Territory Mobility: Willingness to travel up to 50% (local weekly meetings and 2–3 short regional trips per month). Total Rewards at HealthJoy Job Level: 40 We believe high performers deserve competitive pay, true transparency, and real equity in what they build. As a healthcare company, we practice what we preach—delivering top-tier health benefits alongside an aggressive, uncapped sales compensation structure. Target Total Compensation (OTE) $275,000 – $300,000 (Base salary + variable commission, with uncapped upside for overperformance).

How We Think About Pay: Fairness & Transparency: We benchmark compensation using market data, role scope, and candidate experience. Most initial offers land within the mid-range to allow consistent headroom for earnings growth as you perform. Remote-First Pay: HealthJoy is a remote-first workplace. The target range above is our national standard and is not reduced based on your location. Comprehensive Benefits & Ownership: Equity & Ownership: Stock options included so you share in HealthJoy’s long-term growth.

Health & Wellness: Comprehensive medical, dental, and vision plans with an employer HSA match—plus zero-cost access to the HealthJoy navigation platform. Financial Protection: 401(k) with company match, plus fully company-sponsored Short-Term and Long-Term Disability coverage. Life Balance: Flexible PTO and paid parental leave to keep you operating at your best. Commitment to Equal Pay At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive.

We believe that everyone should be paid based on their qualifications, experience, and the work that they do, and not on their gender, race, or any other personal characteristic. Our compensation practices are essential to fostering a diverse and inclusive culture where we value the contributions of all our employees. We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work.

Additionally, we assess the external market and internal equity across like roles. As part of our regular review of pay practices, HealthJoy examines employee pay for potential disparities between persons of different genders, races and ethnicities that are not explainable by objective factors such as performance, experience level, credentials, or location, and are committed to correcting any issues and reviewing practices from unintended outcomes.

Commitment to Equal Opportunity HealthJoy is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other basis forbidden under federal, state, or local law. Don’t meet every single requirement? We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don’t hesitate to apply — we’d love to hear from you.

HealthJoy is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role and HealthJoy, we encourage you to apply. You may be just the right candidate for this or other roles.

Source listing: greenhouse_healthjoy

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