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Regional Vice President; Boston

Remote / Online - Candidates ideally in
Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: HealthJoy
Remote/Work from Home position
Listed on 2026-10-04
Job specializations:
  • Sales
    Business Development, Sales Manager, B2B Sales
Salary/Wage Range or Industry Benchmark: 275000 - 300000 USD Yearly USD 275000.00 300000.00 YEAR
Job Description & How to Apply Below
* Health Joy is a Remote-first company, but the person in this position must reside in/near Boston, MA - with travel up to 50%. Come for the mission. Stay for the experience.

Let’s keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you!

Healthcare benefits are complex, underutilized and a mystery for most users. We’re removing that complexity. Now more than ever, employers are adding value to their employees’ benefits like telemedicine and mental health services. Health Joy’s industry-changing tech platform consolidates those benefits into a simplified benefits experience, saving users time and money.

With over $100M in fundraising to date, and the successful closing of our recent Series D, Health Joy has garnered workplace awards for Inc. 's Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 400 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Sales Team making that happen.

Your

impact.

The Regional Vice President (RVP)-Mid Market (100-3K employees lives) is a proven sales contributor with great energy and initiative to build a territory, drive sales cycles, and close business with the employee benefits broker community. A Health Joy RVP formulates and executes a strategy to maximize sales growth. You are capable of driving outstanding business results and are responsible for generating revenue for his/her assigned region.

Meeting or exceeding quota and activity metrics.

Our sales team members possess the following key behaviors:

  • You take a buyer-centric approach: Drive sales strategies centered around understanding and addressing the unique needs and challenges of employers and employee benefits brokers, ensuring their needs are at the forefront of every interaction.
  • You build trust. You value relationships, and work well within our Health Joy team, and with our internal & external stakeholders.
  • You take ownership. You demonstrate initiative by working your accounts at every stage–you enjoy the chase, the follow up and are relentless in getting to the next step throughout the Sales Journey.
  • You develop a long-term strategy. Adopt a forward-thinking mindset by focusing on building lasting broker relationships and nurturing them over time, emphasizing quality interactions over sheer quantity.
  • You are adaptable to change
    . We're a fast growing company and your ability to be agile and adaptable is key to your success and the success of Health Joy.
  • You are coachable.You appreciate constructive feedback from your manager and leverage resources and training provided by Sales Enablement, Marketing, and Product Marketing to help you be successful.
  • You are a team player
    . You see yourself as part of something larger than yourself. You help execute new strategies, sales decks, talk tracks given by Sales Leadership, Marketing and Enablement so we know what’s working in the market and where we can improve our go-to-market plan of action.
  • You are accountable. We use metrics to help us gauge if we're on the right track. You see activity tracking as your ally to help point you in the right direction.
  • You are creative.You think outside the box and aren’t afraid to try new strategies or trailblaze for the team. You make use of all tools at your disposal in standard and new / different ways.

Our Regional Vice Presidents clearly:

  • Exhibit strong tenacity and a proactive mindset, consistently pursuing broker and employer meetings and taking decisive action to drive results.
  • Possess strong sales discovery skills, adept at uncovering employer and broker needs, pain points, and priorities through…
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