Reports to: CEO | Member, Executive Team | Location: Remote (US)
Starting Base Salary: $287,500 (50th percentile) | 6-Month Salary: $328,660 (65th percentile)
IV. Key ResponsibilitiesA. Executive Leadership & Exec Team Partnership- 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.
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B. Operating Model, Planning & Execution- 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.
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C. Risk, Compliance & Board Engagement- 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.
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D. Talent, Culture & Performance- 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.
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E. Financial Stewardship & Resource Allocation- 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.
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F. AI-Enabled Operations & Scale- 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.
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V. What Success Looks LikeThis 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. 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.
- Organizational outcomes: what the COO owns as a member of the Executive Team
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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.
- Operating dimensions: the levers the COO stewards to deliver the outcomes above
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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 operating infrastructure that lets us capture and grow value, pricing governance and discipline, unit economics (revenue per customer and revenue per patient), and the quality of our financial modeling and dashboarding. Top-line revenue against plan is a commercial (Revenue) outcome; the COO and Finance support it through modeling, process, and visibility rather than owning the number.
VI. Preferred QualificationsWe 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.
Ideal Experience- 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.
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NIce-to-have Experiences- Building or leading AI-forward operating functions.
>- Nonprofit, safety-net, or hybrid revenue / operating-sustainability models.
>- Prior exposure to the safety-net or broader healthcare ecosystem.
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VII. 30 / 60 / 90 Day ObjectivesSpecific targets are set with the CEO in the first few weeks. The milestones below describe the expected trajectory and the kinds of measures we will track at each stage.
First 30 Days: Listen, Learn, and Assess- Complete structured 1:1s with 100% of
