Chief Operating Officer, CareMessage

• You are, first and foremost, a mission-driven operator. You are here because you want to put an operator's craft to work on social impact: building clear plans, an honest cadence, and the accountability to execute them, all in service of patients. Health equity and the safety net are core to why you want this role, not a backdrop to it. We are not looking for a great operator alone; we need someone whose reason for being here is turning operational excellence into greater impact for patients
• CareMessage already has a clear strategy and a strong plan, shaped by a leadership team that has carried it with shared ownership. What we are adding now is a central operating force to support and drive it: someone who brings the cadence, accountability, and follow-through to turn that shared plan into consistent execution. You know that even the best plan is only as good as the discipline behind it. You have run multiple functions, and you understand what a scalable technology business looks like from the inside
• You are a multiplier. You think like a head coach, not a star player: you build teams and an operating model where the collective output far exceeds what the individuals could have produced alone. You coach leaders, set a high bar, and hold it with both empathy and candor
• You are an enterprise integrator. You see the whole organization, not a collection of silos. You clarify roles, decision rights, and cadence; you reduce fragmentation; and you keep the Executive Team and Key Functional Leaders operating as one team with shared priorities rather than functions competing for resources
• You are genuinely forward-thinking about technology. You see AI and automation as the path to scale and quality, not merely cost-cutting, and you have recent, hands-on experience deploying them in an operating context
• You are comfortable leaning into your non-dominant hand, learning the parts of the business that sit outside your original expertise so you can lead them well
• You are a disciplined steward of scarce resources. In a limited-resource, mission-driven environment, you treat every seat and every dollar as a decision in service of patients. You make hard calls, you know what to deprioritize, and you own the tradeoffs clearly
• Throughout, you hold yourself to the highest standard of integrity, you communicate in a way that is clear, open, direct, and kind, and you advocate strongly for well-reasoned positions while remaining genuinely open to being wrong
• You measure every stance against mission impact, not just what is convenient for you or your team
• We are open to a range of backgrounds, including leaders who have held senior roles across several operational functions and those who have gone deep in one area (Finance, People, Compliance and Risk, or Operations) before broadening
• What matters most is the ability to oversee multiple functions effectively, the judgment to lead areas outside one’s original expertise, and the willingness and capacity to build that expertise where it does not yet exist
• If you don’t meet every qualification listed (especially if you come from an under-represented background) but have held senior operating, finance, people, or general-management leadership roles, we strongly encourage you to apply
• 10+ years of multidisciplinary executive experience in strategic leadership across multiple functions
• A technology-organization background, whether tech nonprofit or for-profit tech scaling, with a clear understanding of scalability and services models
• Experience shaping multi-year organizational strategy, not only executing a strategy set by others
• Proven ability to balance mission impact with disciplined business operations
• Experience leading organizations through comparable growth stages (at least beyond 100+ employees)
• Recent, hands-on experience deploying AI and automation in an operating context
• Experience working with executive teams, and ideally with governing boards and board committees
• Superior written and verbal communication, including the ability to present effectively to a Board

Desirable

• CareMessage reaches more than six million patients across nearly 500 safety-net organizations in 45+ states and territories
• We are hiring a Chief Operating Officer (COO) to help shape where CareMessage is headed and to build the operating capacity that turns that strategy into patient impact, so that every dollar and every person is deployed in direct service of health equity
• This is a senior executive role and a full member of the Executive Team, reporting directly to the CEO and serving as a strategic thought partner in shaping the organization's direction
• The COO leads a multi-functional team spanning People Operations, Finance, Compliance and Risk, Operations, and IT, but leads it in service of a larger charge: helping support CareMessage's multi-year strategy and bringing an operating point of view to how we get there
• The mandate is not to grow the organization by adding headcount; it is to build the operating model, systems, and discipline that turn that strategy into a disciplined reality and multiply mission impact, while keeping the team lean, supported, and growing in alignment with our priorities
• Equally important: we need a leader who will own CareMessage's AI strategy for how we operate, not as a cost play, but as a strategic lever for scale and quality
• That means the policies, tooling, workflow adoption, and staffing implications that let us do more with a smaller, more capable team
• The best modern operating leaders are building organizations where technology absorbs routine work and surfaces decisions, freeing people to focus on the highest-judgment, highest-impact work. We expect this person to bring that mindset to CareMessage
• This role partners closely with every function on the Executive Team and with our Key Functional Leaders, serving as the connective tissue between strategy and execution
• Serve as a full member of the Executive Team and a strategic thought partner to the CEO in enterprise planning, decision-making, and organizational performance
• Help shape CareMessage’s multi-year organizational strategy, not only execute it; bring an operating point of view that informs where the organization is headed
• Act as the connective tissue between the Executive Team and our Key Functional Leaders, translating strategy into execution and surfacing tradeoffs clearly
• Drive alignment across functional leaders so the organization executes as one team with shared priorities, not siloed functions competing for resources
• Make and own difficult operational decisions; know when to push and when to yield
• Own the operating plan; ensure functional priorities are resourced, sequenced, and connected to company OKRs
• Translate enterprise strategy into a clear operating rhythm with defined priorities, ownership, and cadence
• Establish disciplined execution practices that reinforce accountability and follow-through across functions
• Build internal systems and processes that scale as the organization grows, without growing the org proportionally
• Own compliance and risk; ensure the organization meets applicable laws, regulations, and internal policies
• Frame enterprise risks, tradeoffs, and sequencing decisions to support effective CEO and Board oversight
• Support Board reporting and committee engagement (including Audit/Compliance, Talent/Compensation, and Finance), including the mission narrative that connects operating performance to our multi-year health-equity mission
• Protect institutional credibility and the trust of our customers, partners, funders, and the communities we serve
• Coach functional leaders to build high-performing teams that produce more together than the sum of their parts
• Hold a high bar on performance; recognize that, in a limited-resource environment, underperformers block mission impact
• Own succession planning and leadership-bench development for the functions you lead
• Foster a culture of trust, transparency, accountability, and continuous improvement
• Partner with Finance on budget performance, resource allocation, forecasting, and long-term operating sustainability
• Treat every seat as a scarce resource in service of the mission; ensure people and dollars are deployed where they move the needle most
• Balance near-term execution demands with long-term organizational health and resilience
• Drive the company’s AI strategy for internal operations: policies, tooling, workflow adoption, and staffing implications
• Identify and implement automation across internal workflows so the team can do more with a smaller, more capable footprint
• Champion an operating culture where technology absorbs routine work and elevates human judgment
• This role is the compass for what a high-functioning CareMessage looks like. The COO's first team is the Executive Team, and the COO owns the organization's outcomes (its mission impact and its OKRs), not the metrics of any single function in isolation
• What Success Looks Like
• Success is a lean, high-performing organization where operational efficiency directly funds greater patient impact: functions connected to company OKRs, an AI-enabled operating model that lets us do more with a smaller and more capable team, and a unified Executive Team and Key Functional Leaders operating as one. The measures below run in that order, the organizational outcomes the COO ultimately owns, then the operating dimensions the COO stewards to produce them
• Mission Impact/Patient Outcomes. This is the ultimate measure, not because the COO owns these patient outcomes directly, but because the output of the COO's output shows up directly in them. The results closest to patients, such as the volume of patients messaged about colorectal cancer screening and comparable clinical-outcome and access KRs, are owned by the teams who run those programs; the COO builds the operating excellence that scales and sustains them. That makes these outcomes the truest signal of whether that excellence is translating into mission, which is why they sit at the top of this list
• Organizational performance and OKR attainment. The COO keeps the whole organization pulling in one direction: ensuring the operating plan and its OKRs ladder up to our strategic vision, clarifying which goals are owned cross-functionally versus by a single department, and resolving the misalignments that surface across teams, so functions execute as one rather than competing for priorities
• People and team. The health and trajectory of the team, through measures like team growth rate, retention, and engagement
• Compliance and risk. The maturation of our compliance and risk posture over time, including audit and control readiness, rather than a narrow set of specific metrics
• Cost and efficiency. How much impact we produce per dollar and per person, through measures like revenue per employee and cost per employee, including progress on AI and automation as the lever to scale impact without scaling headcount proportionally
• Monetization and pricing. The company-level operating infrastructure that helps CareMessage capture and grow value, including pricing governance and discipline, unit-economics visibility such as revenue per customer and revenue per patient, cross-functional operating cadence, and the quality of financial modeling and dashboarding
• Top-line revenue against plan is a commercial/Revenue outcome. The Revenue function owns the revenue number, GTM strategy and execution, pipeline and forecast assumptions, sales and partnerships operating cadence, RevOps processes, and price realization; the COO and Finance support through company-level modeling, resource-allocation discipline, governance, dashboarding, and cross-functional visibility rather than owning the number
• Within 30 Days you will: Listen, Learn, and Assess
• Complete structured 1:1s with 100% of the Executive Team and Key Functional Leaders (roughly 10 to 15 leaders), plus a representative sample of individual contributors across the five functions
• Review every function’s OKRs, budget, and operating cadence, and document a baseline maturity assessment for all five functions (People Operations, Finance, Compliance/Risk, Operations, and IT)
• Inventory the current state of AI and automation across internal workflows, including tooling, adoption, and the largest manual-effort bottlenecks
• Develop a working command of CareMessage’s mission, financial picture, and multi-year strategy
• Within 60 Days you will: Diagnose and Prioritize
• Deliver a written operating diagnostic to the CEO and Executive Team covering 100% of functions: current-state assessment, the top three to five risks, quick wins, and a prioritized set of changes
• Define the top three to five operating priorities, each with a baseline metric and a target
• Stand up or refine the operating cadence: planning rhythm, decision rights, and a reporting calendar
• Align with the Key Functional Leaders on the prioritized changes and on how progress will be measured
• Within 90 Days you will: Plan and Begin Executing
• Land an integrated operating plan tied to company OKRs, with named owners and a cadence, and secure Executive Team and KFL alignment
• Launch a metrics dashboard covering the dimensions in Metrics for the Role (monetization, cost and efficiency, people, compliance, and mission), with baselines established for at least five measures
• Deliver at least one to two quick wins and run the first quarterly operating review
• Launch or refine the first internal AI / automation initiative with explicit adoption milestones (for example, at least one workflow automated or materially streamlined)