Head of Sales

Flagler Health is building the clinical operating system for modern musculoskeletal care. We partner with MSK provider groups and specialty clinics to help them grow, operate more efficiently, and deliver better longitudinal care across patient acquisition, clinical workflows, and ongoing patient engagement. Our platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle. We’ve recently raised our Series B and are entering our next phase of growth. We're hiring a Head of Marketing to build and scale the marketing engine that will drive that growth. This is a pipeline and revenue role. Success means generating high-quality pipeline from the right provider groups, and helping convert that into revenue in a complex, trust-driven market. Role We are hiring a Head of Sales to build and scale a high-performing sales organization and help take the company from early traction to a durable, repeatable revenue engine. Reporting to the Co-Founder & CEO, Albert Katz, this leader will take ownership of the sales function while partnering closely with Marketing (led by our current GTM leader) to drive full-funnel performance. This is not a "sit back and manage" role. As Head of Sales, you will operate as a player-coach—leading from the front in key deals while developing and scaling a team with expectations to continue hiring. You will own company revenue targets, refine and operationalize the sales process, and help evolve the GTM motion to support larger deal sizes, more complex buyer groups, and continued expansion within multi-site provider organizations. This is a high-impact role at a critical inflection point, with the opportunity to shape how Flagler scales its commercial organization. Location: Based in New York City. Key Responsibilities Revenue Ownership: Own company revenue targets and consistently deliver against them. Sales Org Scaling: Lead and scale an existing team of ~8 AEs and SDRs, with responsibility for hiring, onboarding, and developing additional reps as the company grows. Deal Execution: Stay close to the field by leading and closing complex, high-value deals, particularly with multi-site provider organizations. Sales Playbooks: Refine and operationalize repeatable, scalable sales processes to support increasing deal size and complexity. Pipeline Management: Build and manage a healthy pipeline while improving forecasting accuracy and visibility across the funnel. Outbound Strategy: Evolve outbound motions to target high-value provider groups and strategic accounts. Inbound Alignment: Partner closely with Marketing to optimize MQL to SQL conversion, lead quality, and overall funnel efficiency. Contract Negotiation: Lead negotiations for larger, more complex contracts with providers, partners, and other stakeholders. Channel Partnerships: Collaborate with channel and distribution partners to expand market reach and accelerate pipeline generation. Team Leadership: Coach, mentor, and develop sales talent through structured training, deal reviews, and performance management. Hiring & Scaling: Continue building a high-performing sales team with strong culture, accountability, and execution discipline. Tech Discipline: Enforce rigorous CRM usage and sales hygiene to support data-driven decision-making. Customer Voice: Serve as a key conduit between customers and internal teams, informing product and GTM strategy with market feedback. Requirements 6-10+ years of experience in B2B tech sales, with meaningful time in a leadership or player-coach role within high-growth environments. Proven track record of closing complex deals in healthcare, ideally selling into provider organizations such as clinics, specialty groups, or health systems. Experience scaling sales teams and processes beyond early-stage, including managing multiple reps and driving consistent performance. Strong understanding of healthcare workflows, provider economics, and multi-stakeholder buying processes. Demonstrated ability to operate across both strategic and tactical levels—from closing deals to building systems and processes. Experience with pipeline management, forecasting, and sales analytics. Strong negotiation and contract management skills. Comfort working cross-functionally with Marketing, Product, and Leadership teams. Non-Functional Skills & Cultural Fit Charismatic and credible leader who can inspire teams while holding a high performance bar. Thrives in fast-paced, high-growth environments and is comfortable operating through ambiguity. Highly execution-oriented with a willingness to roll up sleeves and stay close to the work. Resilient, adaptable, and competitive, with a strong drive to win. Balances strategic thinking with operational discipline. Reasons to join Flagler Health: Fast-Growing Leader: Join a company with strong momentum and expanding adoption across provider organizations. Leadership Opportunity: Take ownership of and scale a growing sales organization at a critical inflection point. Category Creation: Operate in a large, underserved market with limited direct competition. Compelling Product: Sell solutions with clear ROI, strong adoption, and increasing deal sizes. Meaningful Impact: Help providers improve efficiency, revenue, and patient outcomes. High Earning Potential: Strong compensation tied to company growth and sales performance. Industry Exposure: Build deep relationships across provider organizations and healthcare ecosystems. Compensation & Benefits OTE (cash) : $300,000-$400,000 (comprises base salary + variable bonus). Equity : Competitive equity package. PTO : Flexible paid time off policy. Benefits : Health, dental, vision insurance. Preferences Lives in NYC. Has scaled companies from 0 to $20+ million or 10+ million to $50+ million in a short period of time. Has worked in Healthcare/sold into clinics. Has grit. 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. #J-18808-Ljbffr