Business Operations & Chief of Staff

Job Overview

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.

Responsibilities

Strategic Planning & Management

• 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.

Company & Internal Communications

• 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.

Business Process Development

• 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.

Required Qualifications

• 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.

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.

Benefits

• 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 schedule.
• Commuter Benefits: Convenient options to support your commute needs.
• Professional Development Stipend: A dedicated stipend supports professional development and growth.