Business Operations & Chief of Staff

About Waymark Waymark is a team of healthcare providers, technologists, and builders whose mission is to bring the best healthcare to people with Medicaid benefits. Guided by the communities we serve, we bring support and technology-enabled care to help primary care providers keep Medicaid patients healthy. We are building the tools and designing an approach to enable care to reach the patients who can benefit most. Our core values embody the essence of what makes Waymark a unique team today, and what we look for, nurture, and sustain as a team. We are bold builders, believing that the greatest challenges in care delivery can be solved when we harness the power of community and technology. We are humble learners, seeking feedback and perspectives different from our own, and welcome challenges to our conclusions. We experiment to improve, actively seeking data to inform decisions and to assess our own performance. We act with focused urgency, our commitment to our mission drives us to tirelessly pursue results. If this vision resonates with you, we hope you consider bringing your creativity, your energy, your curiosity to Waymark. About the Role The Business Operations Director & Chief of Staff is a senior contributor responsible for how Waymark plans, communicates, and operates as a company. Reporting directly to the Head of Operations and working closely with the CEO and Executive Leadership Team, this leader owns three interconnected mandates: the company's strategic planning and management system, company and internal communications, and the development of the business processes that keep a scaling organization coordinated and accountable. This role blends the altitude of a strategy leader with the hands-on execution of an operator. You will run the top-level goal-setting processes through which the company sets direction — including company-level planning and performance reviews — and the communications through which that direction reaches every employee. You will design and continuously improve the operating infrastructure the company runs on, from decision-making frameworks to cross-functional workflows. And as a trusted thought partner and proxy for executive leadership, you will take on the ambiguous, high-stakes problems that don't fit neatly within any single function. Responsibilities Strategic Planning & Management Own the company's strategic planning system: refreshing the multi year strategic vision; translating company strategy into clear goals, priorities, and resource allocation decisions; designing and running company-level annual and quarterly planning cycles, rolling up department-level roadmaps and driving key prioritization decisions. Drive the OKR / goal-setting process end to end — objective setting, results consolidation, progress monitoring, and corrective action — ensuring clarity, consistency, and accountability across all teams. Run the executive operating rhythm: leadership team meeting cadence and agendas, d