Head of Sales

Flagler Health•New York, NY

1d•Onsite

About The Position

Flagler Health is building the clinical operating system for modern musculoskeletal care. They 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. Their platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle. The company has recently raised its Series B and is entering its next phase of growth. They 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. This role is focused on pipeline and revenue, generating high-quality pipeline from provider groups and converting it into revenue in a complex, trust-driven market. The Head of Sales will report to the Co-Founder & CEO, Albert Katz, and will own the sales function, partnering closely with Marketing to drive full-funnel performance. This is a player-coach role, leading key deals while developing and scaling a team with expectations to continue hiring. The role involves owning company revenue targets, refining and operationalizing the sales process, and evolving the Go-To-Market 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.

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.

Nice To Haves

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.

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→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.