Senior Sales Executive, Employer Sales
Location: South Florida Preferred | Miami-Dade, Broward & Palm Beach Counties
Additional Locations: Orlando or Tampa, FL
Work Arrangement: Remote, with regional travel
Base Salary:
$90,000–$100,000 Additional Compensation: Uncapped commission + equity eligibility Earning Potential: $300K–$500K for highly successful performers
Language: Bilingual English/Spanish preferred, not required
The Opportunity:
An innovative, venture-backed healthcare startup is looking for a proven Senior Sales Executive to help expand its employer sales business throughout Florida. This company is challenging the traditional employer-sponsored healthcare model, offering businesses a smarter, more flexible alternative to conventional health insurance. This isn't a role where you'll inherit an established book of business or simply manage existing accounts. You'll be joining an early-stage sales organization with the opportunity to develop your own territory, establish relationships, and help shape the company's go-to-market strategy. For the right person, this is an opportunity to get in early, earn significant commissions, participate in equity upside, and potentially grow into a sales leadership position.
What You'll Do:
Build your own pipeline: Identify, prospect, and close new employer clients, primarily businesses with 10–250 employees.
Own the full sales cycle: Manage opportunities from initial outreach and discovery through presentations, negotiations, and closing.
Develop the Florida market: Build relationships throughout South Florida, with an emphasis on Miami-Dade, Broward, and Palm Beach counties.
Sell to decision-makers: Engage business owners, CEOs, CFOs, HR leaders, and benefits decision-makers.
Educate employers: Help companies understand alternative healthcare solutions and how they compare with traditional employer-sponsored health plans.
Build strategic relationships: Develop referral opportunities with brokers, benefits advisors, and other professional partners.
Shape the sales strategy: Collaborate with executive leadership to refine messaging, develop processes, and build a repeatable sales playbook.
Track performance: Maintain accurate pipeline activity, forecasts, and sales reporting using HubSpot.
Help scale the business: Contribute to the company's growth and potentially take on sales leadership responsibilities as the organization expands.
What We're Looking For:- 6+ years of successful, quota-carrying B2B sales experience.
- Proven track record of consistently meeting or exceeding sales quotas.
- Demonstrated ability to generate new business through outbound prospecting and self-sourced opportunities.
- Experience selling directly to small and midsize employers.
- Background in employee benefits, healthcare, health insurance, PEO, payroll, HR technology, or related consultative B2B sales.
- Strong understanding of the employer benefits landscape, ideally including self-funded or level-funded health plans, stop-loss, or alternative healthcare models.
- Experience selling to senior executives and navigating complex buying decisions.
- Established business relationships within the South Florida employer market are highly desirable.
- Bilingual English/Spanish communication skills are preferred but not required.
- Strong consultative selling, relationship-building, negotiation, and closing skills.
- Comfort working independently in an early-stage environment without an established sales playbook.
- Entrepreneurial mindset, high accountability, and a genuine passion for building something from the ground up.
- Preferred Location
- We are prioritizing candidates located in:
- Miami-Dade County: Miami, Coral Gables, Doral, Miami Beach, and surrounding communities.
- Broward County: Fort Lauderdale, Hollywood, Pembroke Pines, Weston, and surrounding communities.
- Palm Beach County: West Palm Beach, Boca Raton, Delray Beach, and surrounding communities.
- Candidates based in Orlando or Tampa will also be considered, although South Florida is strongly preferred.
What Makes This Opportunity Different:
Exceptional earning potential: $90K–$100K base salary, uncapped commissions, and substantial upside for high performers.
Equity participation: Opportunity to share in the long-term success of a growing healthcare company.
Early-stage influence: Work directly with senior leadership and help shape the Florida sales strategy.
Career advancement: Potential to grow into a leadership role as the company expands.
A differentiated product: Bring an innovative healthcare solution to employers looking for alternatives to traditional insurance.
Remote flexibility: Work from home while building meaningful relationships in your market.
Who Will Thrive Here?
This opportunity is best suited for a true new-business hunter who enjoys opening doors, creating opportunities, and closing deals.
You're comfortable building a territory from scratch, prospecting independently, and selling a solution that challenges traditional approaches.
You understand how to engage business owners and executive decision-makers, build trust, and translate complex healthcare solutions into clear business value.
If you're an accomplished sales professional who wants more ownership, more earning potential, and a chance to make an impact at an early-stage company, we'd love to connect.