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Direct Recruiters Inc.

Head of Sales

Direct Recruiters Inc., New York

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Overview

  • Rapidly growing healthcare technology company
  • Uses advanced tools to improve care delivery
  • Broad patient reach and adoption
  • Works with multiple types of healthcare organizations
  • Helps increase efficiency and reduce expenses
  • Distinct business model with limited competition
  • Significant market opportunity ahead

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.

Experience & Skills

Required Experience and Qualifications

  • 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.

Preferred Experience and Qualifications

  • 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.

Compensation

  • PTO: Flexible paid time off policy.
  • Benefits: Health, dental, vision insurance.

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