Flagler Health
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
Fast-Growing Leader: Shape solutions for clinics and hospitals while advancing your career. Leadership Opportunity: Build and lead a sales org 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. 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
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.
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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
Fast-Growing Leader: Shape solutions for clinics and hospitals while advancing your career. Leadership Opportunity: Build and lead a sales org 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. 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
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.
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