Business Operations & Chief of Staff
Job description
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. You will own the design and stewardship of Waymark's multi-year strategic vision and translate that vision into clear, measurable goals, priorities, and resource allocation decisions across the organization. You will drive the end-to-end OKR and goal-setting process, including objective setting, results consolidation, progress monitoring, and corrective action to ensure clarity, consistency, and accountability across all teams. You will run the executive operating rhythm, including leadership team meeting cadence and agendas, decision tracking, quarterly business reviews, and executive offsites. You will provide executive leadership with timely insight and analysis on company performance, surfacing risks, trade-offs, and recommendations to inform key strategic decisions. You will serve as a versatile utility player for the executive team, leading high-priority cross-functional initiatives and special projects that bring structure and momentum to ambiguous problem spaces critical to Waymark's growth. You will own the company's internal communications strategy and calendar, ensuring employees at all levels understand company direction, priorities, progress, and key decisions. You will plan and produce all-company meetings, leadership communications, and company events, handling narrative, content, and logistics. You will draft and edit high-stakes executive communications, including company-wide announcements, strategy narratives, decision memos, and executive presentations. You will co-lead the development of board narratives and decks for quarterly meetings. You will act as a conduit between the executive team and the broader organization, cascading strategic direction downward and channeling feedback, questions, and concerns upward.
Key facts
What you'll do
Lead the development and management of Waymark's multi-year strategic vision and translate it into annual and quarterly plans that clearly articulate priorities and resource allocation. Drive the company's OKR and goal-setting process end to end, from objective setting through results consolidation, progress monitoring, and course correction. Design, own, and iteratively improve the company's operating system, including decision-making frameworks, governance structures, and cross-functional workflows. Plan, produce, and facilitate the executive operating rhythm, including leadership team meetings, decision tracking, quarterly business reviews, and executive offsites. Synthesize complex business data and performance metrics to generate insights and recommendations for executive leadership, highlighting risks, trade-offs, and opportunities. Act as a versatile utility player by leading high-priority, cross-functional initiatives and special projects that require structure, analysis, and execution in critical growth areas. Own the company's internal communications strategy, ensuring employees understand company direction, priorities, progress, and key decisions through consistent and transparent messaging. Plan and produce all-company meetings, leadership communications, and company events, managing narrative, content, and logistics from concept to execution. Draft and edit high-stakes executive communications, including company-wide announcements, strategy narratives, decision memos, and executive presentations. Partner with the Head of Operations to design and refine business processes that enable a scaling organization to remain coordinated and accountable. Serve as a trusted thought partner and executive proxy, taking on ambiguous problems and driving them to resolution with structured analysis and stakeholder alignment. Collaborate closely with the Head of Operations, CEO, and Executive Leadership Team to ensure alignment and execution across all strategic and operational priorities. Support the development of board narratives and decks for quarterly meetings, ensuring clarity, coherence, and data-driven storytelling. Act as a central coordination point for cross-functional work, removing blockers and aligning stakeholders to maintain momentum on critical initiatives. Represent Waymark in external forums and cross-functional partnerships as needed to advance strategic objectives.
Requirements
Demonstrate experience operating at a scaling healthcare or technology company where process and clarity are essential to execution. Show a proven ability to synthesize complex information and translate it into clear strategy, decisions, and communications for executive audiences. Bring strong experience with strategic planning, OKR goal-setting, and performance management frameworks. Exhibit comfort with data, analytics, and qualitative insights to drive decision-making and measure impact. Highlight a track record of owning ambiguous, high-stakes problems and delivering results without direct authority. Demonstrate exceptional written and verbal communication skills, with a portfolio of executive-level narratives, decisions memos, and presentations. Show a bias for action and structured problem-solving, balancing rigorous analysis with timely execution. Bring experience designing and improving operational systems, including governance, workflows, and decision frameworks. Demonstrate the judgment to prioritize among competing initiatives and manage trade-offs in a fast-paced environment. Show evidence of collaborative leadership, influencing without authority and partnering closely with cross-functional peers.
Nice to have
Experience in healthcare, Medicaid, or value-based care environments.
Practical notes
This is a full-time role.
This role may require travel up to 20%.
This role may require short-term visa sponsorship in locations where permitted.
Application review will begin immediately and continue until the role is filled.
Candidates are encouraged to apply as soon as possible to ensure full consideration.
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