Senior Sales Executive

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.