The person in this position must reside in or near Tampa, FL

Come for the mission. Stay for the innovation.

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 and largely underutilized by most people. That’s why HealthJoy was built with one vision: to remove the complexity from being healthy and well. We do that by guiding employees to affordable, high-quality healthcare, consolidating our clients’ health and wellness strategies into the HealthJoy Benefits Operating System - a simple, unified digital experience. The result: healthier employees and a healthier bottom line.

HealthJoy is at the forefront of using AI to transform the healthcare benefits industry. We're building intelligent platforms that use predictive analytics, natural language processing, and machine learning to guide employees to affordable, high-quality care. Our team is passionate about creating a more equitable and understandable benefits experience, while saving our clients time and money.

HealthJoy has garnered workplace awards from Inc. 's Fastest Growing Startups and Built in Chicago’s Best Places to Work, while growing globally to over 300 team members. We’re continuing down the path of high growth and high impact - and this role is one of the most consequential bets we’re making.

Your impact.

You will own the full sales cycle for employers with fewer than 300 employees, from first outreach through signed agreement, and you will book first meetings for our Regional Vice Presidents with larger employers and broker offices. This is a hunting role. Most of your pipeline will come from your own prospecting, with support from marketing and a team of AI agents you manage.

• Prospect small employers and their brokers by phone, email and LinkedIn, and build your own pipeline.
• Run discovery with HR leaders, owners and brokers, and turn what you learn into a clear business case.
• Demo HealthJoy, send proposals, handle objections and close, typically in a few weeks to a few months.
• Book qualified first meetings for RVPs with mid-market and enterprise employers and broker offices.
• Work with brokers as partners: keep them informed and make them look good to their clients.
• Manage a team of AI agents that research accounts, draft outreach and keep Salesforce current, while you own the forecast and every customer conversation.
• Hand new clients to Customer Success with the goals and context they need for a strong launch.

Your experience.

• 2 or more years in a quota-carrying sales role (AE, SDR or BDR) with a record of hitting your number.
• Comfort with high-volume outbound prospecting, including cold calling.
• Strong discovery skills: you ask good questions and listen to the answers.
• Comfort with numbers. You can walk a business owner through costs and savings.
• Disciplined pipeline and CRM habits, and you want to direct AI agents as part of your daily work.
• You live in or will relocate to the Tampa area.
• Experience selling HR, benefits, insurance or health technology to small and mid-sized employers.
• Experience working with or through benefits brokers.
• Familiarity with self-funded health plans.

Total Rewards Job Level: 30

The cash compensation above includes base salary only. Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, overtime pay or other variable incentives.

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.

HealthJoy is a remote-first employer. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled.

At HealthJoy, it is not typical for an individual to be hired at or near the top of the range for their role, and compensation decisions are dependent on the facts and circumstances of each role and individual.

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.