Business Operations & Chief of Staff

Waymark is hiring a Business Operations Director and Chief of Staff to own how the company plans, communicates, and operates. You will report to the Head of Operations and work closely with the CEO and executive team. This role is for someone who can set strategy at the top level and also execute the day-to-day work to make it happen.

What you will do

• Own the company's strategic planning system: refresh the multi-year vision, translate strategy into goals and resource decisions, and run annual and quarterly planning cycles.
• Drive the OKR and goal-setting process from objective setting through progress monitoring and corrective action.
• Run the executive operating rhythm: leadership meeting cadence and agendas, decision tracking, quarterly business reviews, and executive offsites.
• Provide analysis on company performance, surfacing risks, trade-offs, and recommendations.
• Lead high-priority cross-functional initiatives and special projects.
• Own internal communications strategy and calendar, ensuring employees understand direction, priorities, and progress.
• Plan and produce all-company meetings, leadership communications, and company events.
• Draft and edit executive communications: announcements, strategy narratives, decision memos, and presentations.
• Co-lead development of board narrative and decks for quarterly meetings.
• Act as a conduit between the executive team and the organization, cascading decisions and channeling feedback upward.
• Ensure follow-through on decisions made in executive forums.
• Design and improve core operating processes: planning, reporting, decision-making, administration, and cross-functional workflows.
• Own decision-making infrastructure, including decision-memo process, approval workflows, and vendor and procurement review, with Partnerships, Finance, Legal, and Security.
• Identify organizational friction and process gaps; partner with functional leaders to redesign workflows.
• Sustain collaboration processes and tooling, including adoption of AI tools.
• Build lightweight systems for planning, reporting, and accountability that scale.

What they are looking for

• 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.
• Hands-on experience designing and running company-level planning processes, OKRs or equivalent goal frameworks, and performance management rhythms.
• Exceptional written and verbal communication, including executive memos, decks, and company-wide communications.
• Track record of designing and implementing business processes, operating cadences, and decision frameworks.
• Financial and operational modeling skills, combining data-driven analysis with business intuition.
• Ability to influence without authority, build trusted relationships, and handle confidential information with discretion.
• Entrepreneurial self-starter who delivers results without waiting for direction.

Preferred qualifications

• Passion for improving care for Medicaid patients.
• Healthcare experience in value-based care and/or tech-enabled care delivery.
• Comfort with collaboration tools such as Slack, Jira, Confluence, Asana, HubSpot/Salesforce CRM, Jotform, and Google Workspace, plus proficiency with AI tools.
• San Francisco–based preferred.

Pay and benefits

The hiring range varies by location. In San Francisco/Bay Area and New York City: $160,000–$229,000. In Boston, Los Angeles, Seattle, and Washington DC: $147,000–$211,000. In Arlington, Denver, San Diego, and Sacramento: $141,000–$201,000. In Albany, Atlanta, Austin, Baltimore, Central/Southern, Charlotte, Chicago, Dallas/Fort Worth, Detroit, Houston, Las Vegas, Miami, Milwaukee, Philadelphia, Portland, Research Triangle, Salt Lake City, and Twin Cities: $128,000–$183,000. In Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, and Tampa: $124,000–$177,000.

Benefits include stock options, a work-from-home stipend for your first year, medical, vision, and dental coverage, basic life insurance, 20 vacation days accrued over the year plus 11 paid holidays, and 16 weeks of paid parental leave for birthing parents after six months of employment (8 weeks for others).

About Waymark

Waymark is a team of healthcare providers, technologists, and builders working to bring the best healthcare to people with Medicaid benefits. They build tools and design approaches to help primary care providers keep Medicaid patients healthy. Their values include being bold builders, humble learners, experimenting to improve, and acting with focused urgency.