Reports to: CEO | Member of the Executive Team | Location: Remote (US)

Starting base salary: $287,500 (50th percentile) | 6-month salary: $328,660 (65th percentile)

I. Who we’re looking for
CareMessage serves more than six million patients through nearly 500 safety-net organizations across 45+ states and territories. We are hiring a Chief Operating Officer (COO) to shape CareMessage’s direction and build the operational capabilities that turn strategy into measurable patient outcomes—so that every dollar and every person directly advances health equity.

This is a senior executive role and a full position on the Executive Team, reporting directly to the CEO. You will be a strategic partner in defining the organization’s direction. The COO leads a cross-functional team across People Operations, Finance, Compliance and Risk, Operations, and IT—while maintaining focus on a larger purpose: advancing CareMessage’s multi-year strategy and bringing an operational perspective to how we achieve it. This role is not about expanding the organization by hiring additional staff. It is about designing the operating model, systems, and day-to-day discipline that make the strategy a measurable reality—expanding mission impact while keeping the team lean, supported, and aligned with our priorities.

Just as importantly, we need a leader who owns CareMessage’s AI strategy for how we operate—not as a cost-cutting effort, but as a strategic lever to scale both quality and impact. This includes the policies, technology, workflow adoption, and staffing implications that enable us to do more with a smaller, more capable team. The strongest modern operations leaders build organizations where technology handles routine tasks and improves decision-making—freeing people to focus on the highest-judgment, highest-impact work. We expect this mindset to be central to how you lead at CareMessage.

You will work closely with all Executive Team functions and our Key Functional Leaders, serving as the link between strategy and execution.

II. Why this role exists
CareMessage’s next stage of growth requires operational excellence that increases mission impact without adding headcount—and that excellence must be applied across the entire organization, not limited to one area. We are hiring a COO because we need an Executive Team leader who owns how the organization performs against its mission. You will help shape strategy and execute it, convert a shared plan into disciplined execution, and ensure the Executive Team and Key Functional Leaders operate as one team.

The COO strengthens and elevates the internal functions that enable our work, but the goal is larger than simply operating them well. The COO serves as the “compass” for what a high-performing organization looks like—owning operating outcomes and OKRs that connect operational excellence to patient impact; building and sustaining a high-performing team and culture; and safeguarding compliance, risk readiness, and institutional trust so our mission remains durable. That is how we scale impact without scaling costs at the same pace.

III. Who you are
Above all, you are an operator with a mission-first mindset. You want to apply your operational strengths to create social impact by building clear plans, establishing an honest operating rhythm, and driving accountability for results that help patients. Health equity and the safety net are core reasons you want this role. We are not only looking for someone who can operate well—we need someone whose purpose is translating operational excellence into better patient outcomes.

CareMessage already has a clear strategy and a strong plan, supported by a leadership team with shared ownership. What we need now is a central operating force that supports consistent execution—someone who brings cadence, accountability, and follow-through. You understand that strategy only works when it is supported by discipline. You have led multiple functions and understand how to run scalable technology organizations from the inside.

You are a multiplier. You lead more like a head coach than a star performer: you build teams and an operating model where collective results exceed what individuals could accomplish alone. You coach leaders, set high standards, and uphold them with both empathy and candor.

You are an enterprise integrator. You see the organization as a whole—not as separate silos. You clarify roles, decision rights, and cadence; reduce fragmentation; and help ensure the Executive Team and Key Functional Leaders function as one team with shared priorities rather than competing for resources.

You think forward about technology. You see AI and automation as ways to scale quality—not just reduce costs—and you have recent, hands-on experience deploying them in an operating environment.

You are comfortable leading in areas beyond your original expertise and are willing to learn and build capability where needed.

You are a disciplined steward of scarce resources. In a mission-driven environment with limited resources, you treat every role and every dollar as a decision made on behalf of patients. You make difficult tradeoffs, know what to deprioritize, and communicate tradeoffs clearly.

Throughout, you hold yourself to the highest integrity standards. You communicate with clarity, openness, directness, and kindness—while advocating for well-supported positions and staying genuinely open to being wrong.

You measure your decisions by their impact on the mission, not by what is most convenient for you or your team.

IV. Key responsibilities
A. Executive leadership and 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 just execute it—bringing an operational lens to where the organization is headed.
– Connect the Executive Team and Key Functional Leaders, translating strategy into execution and surfacing tradeoffs clearly.
– Ensure functional leaders are aligned so the organization operates as one team with shared priorities instead of siloed functions competing for resources.
– Make and own difficult operational decisions, knowing when to push forward and when to adjust.

B. Operating model, planning, and execution
– Own the operating plan; ensure functional priorities are funded, sequenced, and tied 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 with growth without proportionally increasing the organization.

C. Risk, compliance, and board engagement
– Own compliance and risk; ensure the organization meets applicable laws, regulations, and internal policies.
– Present enterprise risks, tradeoffs, and sequencing decisions to support effective CEO and Board oversight.
– Support Board reporting and committee involvement (including Audit/Compliance, Talent/Compensation, and Finance), including the mission narrative that links operating performance to our multi-year health-equity mission.
– Protect institutional credibility and trust among customers, partners, funders, and the communities we serve.

D. Talent, culture, and performance
– Coach functional leaders to build high-performing teams that outperform what individuals could achieve alone.
– Set and maintain high performance expectations; in a limited-resource environment, underperformance undermines mission impact.
– Own succession planning and leadership pipeline development for the functions you oversee.
– Foster a culture of trust, transparency, accountability, and continuous improvement.

E. Financial stewardship and resource allocation
– Partner with Finance on budget performance, resource allocation, forecasting, and long-term operating sustainability.
– Treat every position as a scarce resource aligned to the mission; ensure people and funding are directed where they make the biggest difference.
– Balance near-term execution needs with long-term health and organizational resilience.

F. AI-enabled operations and scale
– Lead the company’s AI strategy for internal operations, including policies, tools, workflow adoption, and staffing implications.
– Identify and implement automation across internal workflows so the team can do more with a smaller, more capable footprint.
– Build an operating culture where technology handles routine work and enables higher-level human judgment.

V. What success looks like
The COO is the “compass” for what high performance looks like at CareMessage. The COO’s first “team” is the Executive Team. The COO owns organizational outcomes—mission impact and OKR achievement—not performance metrics for any single function. Success means building a lean, high-performing organization where operational efficiency leads directly to greater patient impact: functions aligned to company OKRs, an AI-enabled operating model that delivers more output with a smaller team, and a unified Executive Team and Key Functional Leaders that operate as one.

The measures below reflect that order: first the outcomes the COO owns, then the operating capabilities that enable them.

1. Organizational outcomes (owned by the COO as part of the Executive Team)
Mission impact / patient outcomes
This is the ultimate measure. The COO does not directly deliver patient outcomes, but results reflect how effective the COO’s operational excellence is. The outcomes closest to patients—such as the number of patients messaged about colorectal cancer screening and comparable clinical-outcome and access key results—are owned by the teams running those programs. The COO builds the operational excellence that scales and sustains them, making these outcomes the clearest indicator that excellence is turning into mission impact.

Organizational performance and OKR achievement
The COO ensures the entire organization moves in the same direction by making sure the operating plan and OKRs connect to the strategic vision; clarifying which goals are owned cross-functionally versus by a single department; and resolving misalignment so functions execute together instead of competing for priorities.

2. Operating dimensions (the levers the COO stewards to achieve outcomes)
People and team
Team health and trajectory, measured through indicators such as growth rate, retention, and engagement.

Compliance and risk
Ongoing improvement in compliance and risk readiness over time, including audit and control preparedness.

Cost and efficiency
Impact per dollar and per person, using measures such as revenue per employee and cost per employee, including progress on AI and automation as a lever to scale mission impact without increasing headcount at the same rate.

Monetization and pricing
The operating infrastructure that captures and grows value: pricing governance and discipline, unit economics (revenue per customer and revenue per patient), and strong financial modeling and dashboarding. Reaching revenue targets versus plan is a commercial outcome; the COO and Finance support it through modeling, process, and visibility rather than owning the revenue number alone.

VI. Preferred qualifications
We welcome candidates with a range of backgrounds, including leaders who have held senior roles across multiple operational functions and those who have specialized deeply in one area (Finance, People, Compliance and Risk, or Operations) before expanding. Most important is the ability to lead multiple functions effectively, the judgment to lead beyond your original expertise, and the willingness to build new expertise where it does not yet exist. If you do not meet every listed qualification—especially if you come from an underrepresented background—but you 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.
– Experience with technology organizations (tech nonprofit or for-profit tech scaling), with a clear understanding of scalability and service models.
– Experience shaping multi-year organizational strategy, not just executing plans designed by others.
– Proven ability to balance mission impact with disciplined business operations.
– Experience leading through comparable growth stages (at least beyond 100+ employees).
– Recent hands-on experience deploying AI and automation in an operating environment.
– Experience working with executive teams and, ideally, with governing boards and board committees.
– Strong written and verbal communication, including the ability to present effectively to a Board.

Additional “nice-to-have” experience
– Building or leading AI-forward operating functions.
– Nonprofit experience, safety-net experience, or hybrid models combining revenue with operating sustainability.
– Prior exposure to the safety-net or broader healthcare ecosystem.

VII. 30 / 60 / 90 day objectives
Specific goals will be set with the CEO during the first few weeks. The milestones below outline expected progression and the kinds of measures we will track at each stage.

First 30 days: listen, learn, and assess
– Complete structured one-on-one meetings with 100% of the Executive Team and Key Functional Leaders (about 10–15 leaders), plus a representative group of individual contributors across the five functions.
– Review each 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).
– Assess the current state of AI and automation across internal workflows, including tools, adoption, and the biggest bottlenecks requiring manual effort.
– Build a clear understanding of CareMessage’s mission, financial situation, and multi-year strategy.

First 60 days: diagnose and prioritize
– Deliver a written operating diagnostic to the CEO and Executive Team covering all functions, including the 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 baseline and target measures.
– Set (or refine) operating cadence: planning rhythm, decision rights, and a reporting schedule.
– Align with Key Functional Leaders on the prioritized changes and how progress will be measured.

First 90 days: plan and begin executing
– Finalize an integrated operating plan tied to company OKRs, with named owners and cadence, and secure alignment with the Executive Team and Key Functional Leaders.
– Launch a metrics dashboard covering monetization, cost and efficiency, people, compliance, and mission, establishing baselines 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, including explicit adoption milestones (for example, automate or materially streamline at least one workflow).

Compensation
This is a Chief Operating Officer position and a full member of the Executive Team. The starting base salary is $287,500 per year (50th percentile of the band). If role expectations are met, base compensation increases automatically to the 65th percentile ($328,660 per year) at the six-month mark. Compensation consists of base salary only. We believe in equal pay for equal work. All team members in the same role at the same level are paid the same regardless of geographic location.

Application guidance
As part of an eligible application, you will be asked to answer several key questions. We value responses that are specific and authentic, grounded in real experience and honest reflection. Feel free to omit or anonymize any details you are not comfortable sharing (this applies both here and throughout the interview process).

To support fair and consistent evaluation, we ask candidates not to use AI tools to generate responses. Responses that appear overly generic or not reflective of your voice may not be considered. Out of respect for your time, we encourage responses that take about 1–2 hours total to complete.