*HealthJoy is a Remote-first company, but the person in this position must reside in Southern California, ideally San Diego or LA.

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. HealthJoy’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, HealthJoy 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 Sales Executive (RSE)-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 HealthJoy RSE 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 HealthJoy 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 HealthJoy.
  • 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 sales execs 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 strategic questioning and active listening.
  • Demonstrate executive presence with exceptional presentation, communication and writing skills tailored for engaging with C-suite executives.
  • Comfortably engages in social settings, showcasing adaptability to meet new people and actively participate in diverse interactions. Willingness to step out of your comfort zones and engage with brokers, TPAs, partners, employers, and prospects.
  • Develop their market by creating and fostering new broker relationships and identifying new broker partnerships.
  • Articulate the HealthJoy cost-containment value proposition, demonstrating how our platform impacts employer business outcomes and enhances the healthcare experience for members.
  • Work in partnership within Sales, Marketing, Customer Success, Product and Sales Enablement; therefore cross-company engagement and orchestration is essential. 
  • Meet or exceed assigned sales objectives, monthly, quarterly and annual booking targets by initiating and completing the sales process. This includes broker prospecting, employer lead generation, qualifying opportunities, scheduling broker & employer onsite appointments, delivering presentations, understanding employer benefit challenges, developing solutions and proposals, forecasting, and overcoming objections.
  • Demonstrate a deep understanding of the HealthJoy product offerings and effectively communicate how our solutions can deliver cost-saving benefits to brokers and their clients.
  • Foster productive collaboration across various organizational levels and departments, ensuring positive and effective working relationships.
  • Use Salesforce to track all opportunities, leads, activities, forecasts, etc.
  • Able to learn the complexities of the healthcare, benefits and navigation industries, and can articulate and run demos using our technology.


Your experience.

  • Minimum of (6) years of related field sales experience - ideally, we would like to see this experience as selling directly into benefit broker partners - however, we would consider experience working within HR technology, PEO, healthcare navigation, virtual care services and/or employee benefits or healthcare data analytics as an alternative
  • Demonstrated success in broker channel sales, preferably in employee benefit solutions, with a track record of acquiring new brokerage partnerships.
  • Experience selling to mid-market employers (100-3K employees) is a plus
  • Assertive self-starter with strong relationship management and negotiation skills; skilled at building trust and deepening partner relationships over time
  • Proven track record of consistently achieving sales and revenue goals
  • Strong interpersonal communication skills; excellent poise and presentation skills with a high level of proficiency selling into senior level management benefit brokerage environments
  • Demonstrated proficiency with written and verbal communication
  • Ability to travel up to 40-50% of the time.  Travel will consist of weekly/biweekly local meetings and out of town travel once or twice a month for 2-4 days in your assigned territory. 


Total Rewards Job Level: 40

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance. 

Base salary: $105,000 to $130,000 plus variable

In addition to cash compensation, HealthJoy offers a rich “Total Rewards” package that includes:

  • Medical, Dental and vision insurance packages
  • HSA contribution match
  • Stock options for eligible roles
  • 401k match
  • Paid parental leave
  • Company sponsored Short Term and Long Term Disability coverage
  • Flexible PTO 

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.

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