Chief Operating Officer

CareMessage

5d • Remote

About The Position

CareMessage is seeking a Chief Operating Officer (COO) to join its Executive Team. This senior executive role reports directly to the CEO and is responsible for building the operating capacity to achieve the organization's strategy and patient impact goals. The COO will lead teams in People Operations, Finance, Compliance and Risk, Operations, and IT, focusing on building an operating model, systems, and discipline that turns strategy into reality and multiplies mission impact while keeping the team lean. A key aspect of this role is owning CareMessage's AI strategy for operations, leveraging technology to absorb routine work and free up staff for higher-judgment tasks. The COO acts as the connective tissue between strategy and execution, partnering closely with all functions on the Executive Team.

Requirements

• Mission-driven operator with a passion for social impact and health equity.
• Experience running multiple functions and understanding scalable technology businesses.
• Ability to act as a multiplier, building teams and operating models where collective output exceeds individual contributions.
• Experience as an enterprise integrator, seeing the whole organization and clarifying roles, decision rights, and cadence.
• Forward-thinking about technology, with recent, hands-on experience deploying AI and automation in an operating context.
• Comfort leaning into non-dominant areas of expertise to lead them well.
• Disciplined steward of scarce resources, making hard calls and owning tradeoffs.
• High standard of integrity, clear, open, direct, and kind communication.
• Ability to measure every stance against mission impact.
• 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).
• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• Starting Base Salary: $287,500 (50th percentile)
• 6-Month Salary: $328,660 (65th percentile)
• Compensation structured as base salary.
• Equal work for equal pay.
• All team members performing the same role at the same level are paid the same, regardless of geographic location.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed