Head of Sales

Flagler Health is a fast-growing healthtech company transforming how healthcare organizations deliver care through AI-powered workflow automation, remote patient engagement, and chronic care programs. Our platform has already served over 1.5 million patients and is trusted by providers and payers to improve efficiency, lower costs, and drive better outcomes. With a unique freemium model and minimal direct competition, we are poised to capture a large share of the $4.5T U.S. healthcare industry.

Role

We are now making our first Sales leadership hire to build a scalable, high-performing sales organization and take the company from founder-led sales to a repeatable, metrics-driven GTM engine.

Reporting to the Co-Founder & CEO, Albert Katz, this is not a “sit back and manage” role. As our Head of Sales, you’ll be a player-coach—closing deals yourself while building and mentoring a world-class team of AEs and SDRs. You’ll own company revenue targets, design and enforce a disciplined sales process, and work closely with Marketing and Product to shape commercial strategy. This is a rare chance to join a company at an inflection point and directly influence growth and market leadership.

Key Responsibilities

• Revenue Ownership: Own company revenue targets and consistently deliver against them.

• Organizational Transition: Lead the shift from founder-led sales to a self-sufficient, high-performing sales org.

• Deal Execution: Travel extensively to meet prospects, close deals, and build long-term customer relationships.

• Sales Playbooks: Develop repeatable, scalable sales processes and playbooks.

• Pipeline Management: Forecast pipeline and revenue with precision.

• Outbound Strategy: Design and execute outbound sales motions.

• Inbound Alignment: Partner with Marketing to optimize MQL→SQL conversion and inbound lead flow.

• Contract Negotiation: Negotiate enterprise-level contracts with providers, payers, and partners.

• Channel Partnerships: Build and manage channel partner relationships to expand market reach.

• Team Leadership: Train, mentor, and develop AEs and SDRs through weekly sessions.

• Hiring & Scaling: Build and scale a high-performing sales team, instilling a culture of accountability and grit.

• Tech Discipline: Enforce rigorous CRM usage to maintain clean data and accountability.

• Customer Voice: Serve as the voice of the customer, relaying market insights to leadership and product teams.

Requirements

• 6+ years of experience in B2B tech sales, with ~2 years in a player/coach leadership role within high-growth startup environments.

• Proven track record of closing enterprise-level healthtech deals with domain relevance (clinics, provider groups, health systems).

• Strong negotiation and contract management experience.

• Demonstrated ability to design and enforce disciplined GTM processes.

• Deep knowledge of healthcare: provider and payor economics, stakeholder mapping, regulatory considerations, and healthcare org pain points.

• Tech-savvy and analytics-driven with experience building pipeline forecasts and revenue models.

• Skilled in pricing, ICP definition, segmentation, and sales operations.

• Strong people management and training skills.

Non-Functional Skills & Cultural Fit

• Charismatic leader who can inspire while holding teams accountable.

• Thrives in ambiguity and fast-changing startup environments—knows that “death is always around the corner.”

• Resilient, adaptable, and relentlessly gritty.

• Gets things done: rolls up sleeves, fills gaps, and executes.

• Strategic thinker with strong execution discipline.

• Hates losing and competes with urgency.

Reasons to join Flagler Health:

1. Fast-Growing Leader: Shape solutions for clinics and hospitals while advancing your career.

2. Leadership Opportunity: Build and lead a sales org from the ground up.

3. Untapped Market, No Competition: Innovate freely in a white-space market.

4. Valuable, Freemium Products: Sell tools with clear ROI and low barriers to adoption.

5. Meaningful Impact: Help providers save time and improve patient outcomes.

6. High Earning Potential: Strong commissions tied to a growing pipeline.

7. Cutting-Edge Tools: Access advanced CRM, analytics, and training systems.

8. Industry Network Growth: Build relationships with hospital administrators and clinicians.

• OTE (cash): $250,000-$450,000 (comprises base + variable bonus).

• Equity: Competitive equity package.

• PTO: Flexible paid time off policy.

• Benefits: Health, dental, vision insurance.

Our values

This is what you can expect of your teammates at Flagler:

• Persistence + ownership of outcomes: We wear many hats and aren’t afraid to run through walls to solve hard problems.

• Personal + professional growth: We push ourselves to learn new things and embrace challenges, even if it means that we sometimes fail.

• Don’t take things personally: We value and react quickly to constructive feedback.

• Speed is our ally: In the fast-paced world of startups, we understand the value of moving swiftly. We thrive on the adrenaline of working rapidly.

• Be Right: We are highly detailed oriented and try to be right, a lot.