Head of Sales

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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 optimise 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

Non‑Functional Skills & Cultural Fit

Reasons to join Flagler Health

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