Director of Sales

This is a critical leadership position with ownership over hiring, developing and mentoring the team, running Deal Desk and Revenue Operations, and ensuring that how we sell is disciplined, predictable, and scalable. You will report to the Chief Revenue Officer and play a foundational role in shaping CareMessage’s commercial engine as we grow. 

Who You Are 

You are a senior commercial leader who owns revenue outcomes, not just process. You are comfortable carrying a personal quota, while also leading execution through other sellers, and you bring firsthand experience closing SaaS deals in healthcare involving nuanced understanding of the market. You think in systems and standards rather than one-off heroics, using structure and discipline to raise performance across the sales organization. You coach, unblock, and elevate the sellers around you, bringing calm, clarity, and decisiveness to ambiguous situations. Most importantly, you are motivated by building sustainable revenue models that support long-term health equity impact.

Key Responsibilities

• Sales Execution Leadership
• Own sales execution outcomes across new business, renewals, and expansion for FQHC, FCC, and Tribal Health Market.
• Be accountable for $2M in new ARR and 101% Net Revenue Retention.
• Provide execution leadership, coaching, and deal support to Growth Managers.
• Set standards for pipeline management, deal strategy, account planning, and forecasting.
• Step directly into priority or complex deals when needed.
• Use frontline deal experience to continuously improve sales processes and enablement.
• Attend regional conferences and collaborate with state-based partners to develop opportunities, partnerships, and pipeline.
• Personal Sales Execution
• Personally own and close at least $500K in new Core Business ARR annually.
• Lead complex, high-stakes, or strategically important deals from discovery through close.
• Model best-in-class sales execution, negotiation, and account strategy.
• Translate firsthand selling insights into improvements in pricing, messaging, and tooling.
• Deal Desk & Commercial Governance
• Own Deal Desk operations, including pricing review, discounting strategy, contract structure, and approval workflows.
• Partner with Chief Revenue Officer, finance, or compliance to ensure deals meet margin, compliance, and risk standards while maintaining velocity.
• Define approval thresholds, escalation paths, and exception frameworks.
• Ensure consistent deal quality across all Growth Managers.
• Revenue Operations & Systems Ownership
• Own the commercial RevOps spine across tools and workflows (CRM, forecasting, approvals, reporting).
• Ensure data integrity across pipeline, bookings, ARR, subsidies, and renewals.
• Partner with Chief Revenue Officer and RevOps lead on forecasting accuracy and revenue modeling.
• Identify friction across the revenue lifecycle and drive process improvements.
• Sales Operations & Enablement
• Collaborate with Chief Revenue Officer on sales operations inputs including territory design, quota inputs, capacity planning, and compensation support.
• Partner with Growth Marketing on sales enablement.
• Develop onboarding, ramp, and training for Growth Managers.
• Equip sellers with clear pricing guidance, messaging, competitive context, and deal tools.
• Performance Indicators (KPIs)
• New business revenue attainment ($2M total; $500K personal)
• Net Revenue Retention (101%)
• Deal velocity and close rates
• Forecast accuracy and pipeline health
• Growth Manager productivity and readiness

Requirements

• 8–12+ years of experience in SaaS sales, sales leadership, or revenue operations.
• 5+ years managing a team of 3+ AEs selling software in the healthcare as Director of Sales.
• Proven experience owning a personal quota while leading execution through other sellers.
• Strong background in pricing strategy, contract negotiation, and complex deals.
• Analytical, systems-oriented approach to revenue execution.
• Ability to lead cross-functionally without formal authority.
• Self-motivated, professional, confident, flexible, and results-driven
• Willing to travel as required .
• Alignment with CareMessage’s mission to advance health equity.

Recommended Experience

• Experience working with healthcare technology, SaaS, or regulated markets
• Experience with FQHCs or other safety-net organizations
• Familiarity with nonprofit, safety-net, or hybrid revenue models.
• Experience with HubSpot, Gainsight, Gong, etc
• Background in scaling or transformation-stage organizations.