Business Operations & Chief of Staff

echnologists, 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 embody the essence of what makes Waymark a unique team today, and what we look for, nurture, and sustain as a team. 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, our commitment to our mission drives us to tirelessly pursue results. If this vision resonates with you, we hope you consider bringing your creativity, your energy, your curiosity to Waymark. About the Role The 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 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. Responsibilities Strategic Planning & ManagementOwn 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 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.Company & Internal CommunicationsOwn 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.Process DevelopmentDesign, 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. Required Qualifications Experience: 7+ years in 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 processes, operating cadences, and decision frameworks that improve organizational execution.Analytical Rigor: Financial and operational modeling skills, combining data-driven analysis with sound 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. Preferred Qualifications Passion for improving care for Medicaid patients.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.San Francisco–based preferred Hiring Range US Employees in San Francisco/Bay Area, New York City - $160,000 - $229,000 US Employees in Boston, Los Angeles, Seattle, Washington DC - $147,000 - $211,000 US Employees in Arlington, Denver, San Diego, Sacramento - $141,000 - $201,000 US Employees 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, Twin Cities - $128,000 - $183,000 US Employees in Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, Tampa - $124,000 - $177,000 In addition to salary, we offer a comprehensive benefits package. Here’s what you can expect: Stock Options: Opportunity to invest in the company’s growth. Work-from-Home Stipend: A dedicated stipend for your first year to help set up your home office. Medical, Vision, and Dental Coverage: Comprehensive plans to keep you and your family healthy. Life Insurance: Basic life insurance to give you peace of mind. Paid Time Off: 20 vacation days, accrued over the year, plus 11 paid holidays. Parental Leave: 16 weeks of paid leave for birthing parents after six months of employment, and 8 weeks of bonding leave for non-birthing parents. Retirement Savings: Access to a 401(k) plan with a company contribution, subject to a vesting . Commuter Benefits Convenient options to support your commute needs. Professional Development Stipend: A dedicated stipend supports professional development and growth. 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. 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. Waymark is dedicated to building a supportive, equal opportunity, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every preferred qualification in the job , we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings! Skills: Product & Operations