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 include:

• 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, driven by our commitment to our mission and results.

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 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 top-level goal-setting processes, company-level planning and performance reviews, communications, operating infrastructure, decision-making frameworks, cross-functional workflows, and ambiguous high-stakes problems.

Responsibilities:

Strategic Planning & Management:

• Own the company's strategic planning system, including multi-year strategic vision, company strategy, goals, priorities, resource allocation, annual and quarterly planning cycles, department-level roadmaps, and prioritization decisions.
• Drive the OKR and goal-setting process end to end, including objective setting, results consolidation, progress monitoring, corrective action, clarity, consistency, and accountability.
• Run the executive operating rhythm, including 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.
• Lead high-priority cross-functional initiatives and special projects, bringing structure and momentum to ambiguous problem spaces.

Company & Internal Communications:

• Own the company's internal communications strategy and calendar.
• Plan and produce all-company meetings, leadership communications, and company events.
• Draft and edit executive communications, including company-wide announcements, strategy narratives, decision memos, and executive presentations.
• Co-lead development of board narratives and decks for quarterly meetings.
• Act as a conduit between the executive team and broader organization, cascading decisions and strategic direction and channeling feedback upward.
• Ensure follow-through on decisions and commitments made in executive forums.

Business Process Development:

• Design, implement, and continuously improve core operating processes for planning, reporting, decision-making, administration, and cross-functional coordination.
• Own decision-making infrastructure, including decision memos, approval workflows, and vendor and procurement review, in partnership with Partnerships, Finance, Legal, and Security.
• Identify organizational friction, process gaps, and duplicated effort; redesign workflows and clarify ownership with functional leaders.
• Improve collaboration processes and tooling, including thoughtful adoption of AI tools.
• Build lightweight systems for planning, reporting, and accountability that scale with the company.

Required Qualifications:

• 7+ years in business operations, chief of staff, strategy, or consulting roles with direct healthcare experience.
• Success operating at the executive level in a fast-paced, high-growth environment.
• Expert-level proficiency with PowerPoint deck creation and Excel modeling.
• Experience designing and running company-level planning processes, annual and quarterly planning, OKRs or equivalent goal frameworks, and performance management rhythms.
• Exceptional written and verbal communication, including executive memos, decks, and company-wide communications.
• Ability to distill complex concepts into clear narratives for executive and all-employee audiences.
• Experience 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, handle confidential information with discretion, and deliver results independently.

Preferred Qualifications:

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

Hiring Range:

• US employees in San Francisco/Bay Area and New York City: $160,000 - $229,000.
• US employees in Boston, Los Angeles, Seattle, and Washington DC: $147,000 - $211,000.
• US employees in Arlington, Denver, San Diego, and Sacramento: $141,000 - $201,000.
• US employees in listed metropolitan areas including Atlanta, Austin, Chicago, Dallas/Fort Worth, Houston, Miami, Philadelphia, Portland, and Salt Lake City: $128,000 - $183,000.
• US employees in listed metropolitan areas including Indianapolis, Nashville, Phoenix, Pittsburgh, St. Louis, and Tampa: $124,000 - $177,000.

Benefits:

• Stock options.
• Work-from-home stipend.
• Medical, vision, and dental coverage.
• Life insurance.
• Paid time off, including 20 vacation days and 11 paid holidays.
• Parental leave.
• Retirement savings with a 401(k) company contribution.
• Commuter benefits.
• Professional development stipend.

Offer of employment is contingent upon successful completion of a background check, including employment history and advanced degree verification when applicable.

Waymark is dedicated to building a supportive, equal opportunity, and accessible workplace that fosters a sense of belonging.