Business Operations & Chief of Staff

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.

- 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, decision tracking, quarterly business reviews, and executive offsites.

- Provide executive leadership with insight and analysis on company performance, surfacing risks, trade-offs, and recommendations to inform key decisions.

- Serve as a versatile utility player for the executive team: lead high-priority cross-functional initiatives and special projects, bringing structure and momentum to ambiguous problem spaces critical to Waymark's growth.

- Own the company's internal communications strategy and calendar, ensuring employees understand company direction, priorities, progress, and key decisions.

- Plan and produce all-company meetings, leadership communications, and company events - narrative, content, and logistics.

- Draft and edit high-stakes executive communications: company-wide announcements, strategy narratives, decision memos, and executive presentations.

- Co-lead the development of board narrative / decks for quarterly meetings.

- Act as a conduit between the executive team and the broader organization - cascading decisions and strategic direction downward and channeling feedback, questions, and early signals of misalignment upward.

- Ensure follow-through on decisions and commitments made in executive forums, routing actions to the right owners and driving them to closure.

- Design, implement, and continuously improve the core operating processes that keep the company coordinated as it scales - planning, reporting, decision-making, administration, and cross-functional coordination workflows.

- Own the company's decision-making infrastructure, including decision-memo process, approval workflows, and vendor and procurement review, in partnership with Partnerships, Finance, Legal, and Security.

- Identify organizational friction, process gaps, and duplicated effort; partner with functional leaders to redesign workflows and clarify ownership.

- Sustain and improve the company's collaboration processes and tooling to maximize productivity and coordination across teams, including thoughtful adoption of AI tools.

- Build lightweight systems for planning, reporting, and accountability that scale with the company without adding unnecessary process.

- Experience: 7+ years in business operations, chief of staff, strategy, or consulting roles with direct healthcare experience; demonstrated success operating at the executive level in a fast-paced, high-growth environment; expert-level proficiency with PowerPoint deck creation and Excel modeling.

- Strategic Planning: Hands-on experience designing and running company-level planning processes - annual/quarterly planning, OKRs or equivalent goal frameworks, and performance management rhythms.

- Communication: Exceptional written and verbal communication, including executive memos, decks, and company-wide communications; able to quickly distill complex concepts into clear, compelling narratives for executive and all-employee audiences.

- Process & Systems Thinking: Track record of designing and implementing business processes, operating cadences, and decision frameworks that improve organizational execution.

- Analytical Rigor: Financial and operational modeling skills, combining data-driven analysis with sound business intuition to pressure-test decisions on contracting, budgeting, and strategy.

- Influence & Judgment: Ability to influence without authority, build trusted relationships across all levels, and handle confidential information with discretion; entrepreneurial self-starter who delivers results without waiting for direction.

- Healthcare experience in value-based care and/or tech-enabled care delivery.

- Comfort with a range of collaboration tools (Slack, Jira, Confluence, Asana, HubSpot/Salesforce CRM, Jotform, Google Workspace) and proficiency with AI tools.