Business Operations & Chief of Staff, Waymark

• 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
• Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that some of us may be less likely to apply to jobs unless we meet every single qualification

Desirable

• 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

• Offer of employment is contingent upon successful completion of a background check. Employment history and advance degree verification (when applicable) are included as part of the standard background check process