Head of Sales - Remote

Overview

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.

In Short

• Own company revenue targets and consistently deliver against them.
• Lead the shift from founder-led sales to a self-sufficient, high-performing sales organization.
• Travel extensively to meet prospects, close deals, and build long-term customer relationships.
• Develop repeatable, scalable sales processes and playbooks.
• Forecast pipeline and revenue with precision.
• Design and execute outbound sales motions.
• Partner with Marketing to optimize MQL→SQL conversion and inbound lead flow.
• Negotiate enterprise-level contracts with providers, payers, and partners.
• Build and manage channel partner relationships to expand market reach.
• Train, mentor, and develop AEs and SDRs through weekly sessions.

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.
• Strong negotiation and contract management experience.
• Demonstrated ability to design and enforce disciplined GTM processes.
• Deep knowledge of healthcare and related economics.
• Tech-savvy and analytics-driven with experience building pipeline forecasts.
• Skilled in pricing, ICP definition, segmentation, and sales operations.
• Strong people management and training skills.

Benefits

• Fast-Growing Leader: Shape solutions for clinics and hospitals while advancing your career.
• Leadership Opportunity: Build and lead a sales organization from the ground up.
• Untapped Market, No Competition: Innovate freely in a white-space market.
• Valuable, Freemium Products: Sell tools with clear ROI and low barriers to adoption.
• Meaningful Impact: Help providers save time and improve patient outcomes.
• High Earning Potential: Strong commissions tied to a growing pipeline.
• Cutting-Edge Tools: Access advanced CRM, analytics, and training systems.
• Industry Network Growth: Build relationships with hospital administrators and clinicians.