Director, Enterprise Sales

Director, Enterprise Sales

Company: Brightree Location: USA Work Model: Onsite Contract: Permanent

About the Role

Brightree is seeking a senior sales leader to join their team as the Director of Enterprise SaaS Sales. This executive role is responsible for driving new enterprise revenue, expanding strategic healthcare accounts, and building a high-performing sales organization. The ideal candidate will possess deep enterprise SaaS sales expertise combined with a working knowledge of healthcare provider, payer, and regulated healthcare markets. This position involves owning complex, multi-stakeholder sales cycles and serving as a trusted advisor to C-suite healthcare executives.

Key Responsibilities

• Revenue & Growth Leadership:
  • Own and deliver enterprise Annual Recurring Revenue (ARR) targets across new logo acquisition and strategic account expansion within healthcare markets (e.g., providers, payers, HME/DME, pharmacy, health systems).
  • Drive predictable pipeline generation, accurate forecasting, and disciplined deal execution.
  • Lead large, complex sales cycles (6–18 months) involving multiple decision-makers, clinical, IT, finance, and compliance stakeholders.
• Team Leadership & Development:
  • Recruit, coach, and lead a team of high-performing Enterprise Account Executives and sales managers.
  • Establish repeatable enterprise selling motions aligned with proven SaaS methodologies (e.g., Challenger, Korn Ferry Sell, MEDDICC).
  • Set clear performance expectations, conduct regular deal reviews, and develop next-generation sales leadership talent.
• Healthcare-Informed Selling:
  • Translate healthcare industry challenges—regulatory, reimbursement, interoperability, outcomes, and cost pressures—into compelling SaaS value propositions.
  • Demonstrate fluency in healthcare workflows, data privacy (HIPAA), and buyer personas across clinical, operational, and IT functions.
  • Partner with Product, Marketing, and Customer Success to refine healthcare-specific messaging, use cases, and Return on Investment (ROI) narratives.
• Strategic Account & Executive Engagement:
  • Build and maintain executive-level relationships with enterprise healthcare customers and prospects.
  • Personally engage in high-value opportunities, executive presentations, and contract negotiations.
  • Act as the voice of the customer internally, influencing roadmap priorities and go-to-market strategies.
• Cross-Functional Leadership:
  • Collaborate closely with Sales Operations, Marketing, Implementation, and Customer Success to ensure seamless handoffs and long-term customer value.
  • Partner with Finance and Legal on enterprise pricing, contracting, and revenue recognition considerations.
  • Support industry events, conferences, and executive forums as a senior commercial leader.

Requirements

• Bachelor’s degree, MBA, or equivalent experience required.
• 10+ years of progressive SaaS sales experience, with at least 5 years in enterprise or strategic account leadership roles.
• 3–5 years of hands-on people leadership experience, with a demonstrated ability to inspire, mentor, and guide teams while cultivating a positive, inclusive, and results-driven culture.
• Demonstrated success selling complex, mission-critical SaaS solutions into healthcare or adjacent regulated industries.
• Proven ability to build, scale, and lead enterprise sales teams with consistent quota attainment.
• Strong executive presence with the ability to influence C-suite and board-level stakeholders.
• Deep understanding of value-based selling, ROI modeling, and long-term account strategy.
• Experience navigating healthcare buying committees, compliance considerations, and extended sales cycles.

What We Offer

• A data-driven, customer-centric approach to SaaS leadership.
• The opportunity to blend strategic thinking with hands-on execution.
• Credibility to engage healthcare executives and the rigor to run an enterprise sales operation.
• Leadership maturity to scale teams while driving sustained growth.
• A comprehensive benefits package including medical, vision, dental, life insurance, disability insurance, Health Savings Account (HSA), Flexible Spending Account (FSA), 401(k), Employee Stock Purchase Plan (ESPP), Employee Assistance Program (EAP), and tuition assistance.
• Generous Paid Time Off (PTO), paid holidays, and floating days.
• Caregiver leave for welcoming new family members.
• Competitive salary range: $176,000 - $220,000 (individual pay decisions are based on various factors such as geographic work location, relevant qualifications, work experience, and skills).
• A supportive and inspiring work environment focused on creating a healthier world.
• A culture driven by excellence, encouraging individual expression, and valuing innovative ideas.