Director of Sales, CareMessage

• 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
• 8–12+ years of experience in SaaS sales, sales leadership, or revenue operations
• 3+ years managing a team of 3+ AEs selling software in the healthcare
• 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
• Note: If you don’t fit this description perfectly (in particular, if you come from an under-represented group) but have held sales lead roles in the past, please apply!
• This role is a Lead-level position, equivalent to a senior individual contributor who has held progressively scoped Sales Lead or revenue leadership roles with increasing ownership, influence, and impact across sales execution and operations

Desirable

• We are hiring a Director of Sales to own sales execution and sales outcomes across new business, renewals, and expansion, while also personally closing a meaningful portion of revenue
• This role will lead a high-performing team of Growth Managers, who responsible for selling CareMessage solutions
• This role is accountable for ensuring CareMessage consistently meets its revenue and expansion goals
• The Director of Sales blends hands-on selling with execution leadership and operational ownership
• This role will play a pivotal role in shaping our go-to-market strategy, is accountable for $2M in new business and a 101% Net Revenue Retention target
• 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
• 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