Sales Lead, 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 complex SaaS deals involving nuanced pricing, contracting, and multi-stakeholder negotiations
• 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
• 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
• Alignment with CareMessage’s mission to advance health equity
• Of $252,166 p

Desirable

• We are hiring a Sales Lead (L4) to own sales execution outcomes across new business, renewals, and expansion, while also personally closing a meaningful portion of revenue
• This role operates through a team of L3 Growth Managers, who own day-to-day account execution, and is accountable for ensuring CareMessage consistently meets its revenue and retention goals
• The Sales Lead blends hands-on selling with execution leadership and operational ownership
• This role is accountable for $2M in new business and a 101% Net Revenue Retention target, with the expectation that the Sales Lead will personally close new ARR and drive the remainder through Growth Managers
• In parallel, this role owns Deal Desk and Revenue Operations, and Sales Enablement, ensuring that how we sell is disciplined, predictable, and scalable
• You will report to the Chief Customer and Revenue Officer and play a foundational role in shaping CareMessage’s commercial engine as we grow
• Own sales execution outcomes across new business, renewals, and expansion
• Be accountable for $2M in new ARR and 101% Net Revenue Retention
• Provide execution leadership, coaching, and deal support to L3 Growth Managers, who own day-to-day account execution
• 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
• Personally own and close at least $750K in new 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
• 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
• 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
• Collaborate with Chief Revenue Officer on sales operations inputs including territory design, quota inputs, capacity planning, and compensation support
• Own sales enablement in partnership with Growth Marketing and Product Marketing
• Develop onboarding, ramp, and ongoing training for Growth Managers
• Equip sellers with clear pricing guidance, messaging, competitive context, and deal tools
• New business revenue attainment ($2M total; $750K personal)
• Net Revenue Retention (101%)
• Deal velocity and close rates
• Forecast accuracy and pipeline health
• Growth Manager productivity and readiness
• This is a Lead-level individual contributor role
• The initial focus is on execution excellence and leverage through systems, standards, and cross-functional leadership, not immediate people management
• As the revenue organization scales, this role is expected to transition into direct people management, with responsibility for Growth Managers and Sales Operations
• Progression will be based on demonstrated ability to scale revenue, build durable operating systems, and lead execution through others
• 30 Days
• Master CareMessage’s product portfolio, roadmap, and user workflows
• Conduct initial customer interviews across key segments
• Learn CareMessage’s sales motion, pricing models, subsidy mechanics, and contract standards
• Audit Deal Desk, RevOps systems, forecasting, and approval workflows
• Begin carrying pipeline and supporting active deals
• Establish operating cadence with Growth Managers and cross-functional partners
• 90 Days
• Fully own sales execution outcomes and Deal Desk operations
• Actively close deals toward the $750K personal target
• Improve deal workflows, pipeline hygiene, and forecasting accuracy as needed
• Make improvements to enablement for pricing, deal strategy, and pipeline management as needed
• 180 Days
• Demonstrate progress toward $2M in new business and 101% NRR
• Consistently close personal quota while scaling execution through Growth Managers
• Institutionalize repeatable sales, deal, and forecasting processes
• Influence annual planning inputs (quotas, capacity, compensation)
• Operate as the clear execution leader for the sales organization