Chief of Staff, Business Operations

Waymark

Business operations and Chief of Staff leader scaling Medicaid healthcare delivery at Waymark. Owning strategic planning, executive communications, operating systems, and high-priority cross-functional initiatives.

Posted 8/7/2026full-timeRemote • 🇺🇸 United StatesLead💰 $124,000 - $229,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in strategic planning, including OKR implementation, performance analysis, and cross-functional initiative leadership. Proficient in executive communication and collaboration processes, with a strong focus on healthcare operations and decision-making frameworks.

Highest-signal resume keywords

Strategic PlanningOKR ImplementationExecutive CommunicationFinancial ModelingHealthcare Operations

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

PowerPoint Deck CreationExcel ModelingBusiness Process DesignPerformance ManagementData-Driven Analysis

Soft Skills

Exceptional Written CommunicationInfluencing Without AuthorityBuilding Trusted RelationshipsEntrepreneurial Self-Starter

Tools & Technologies

SlackJiraConfluenceAsanaHubSpot/Salesforce CRMGoogle WorkspaceAI Tools

Industry Keywords

Healthcare ExperienceValue-Based CareTech-Enabled Care Delivery

About the role

Key responsibilities & impact

Own Waymark’s strategic planning system, including multi-year vision, company goals, resource allocation, annual and quarterly planning, and department roadmap rollups.
Drive the OKR/goal-setting process, including objective setting, results consolidation, progress monitoring, and corrective action.
Run the executive operating rhythm, including leadership meetings, decision tracking, quarterly business reviews, and executive offsites.
Provide executive leadership with company performance analysis, risks, trade-offs, and recommendations.
Lead high-priority cross-functional initiatives and ambiguous special projects.
Own the internal communications strategy and calendar.
Plan and produce all-company meetings, leadership communications, and company events.
Draft and edit executive communications, strategy narratives, decision memos, and presentations.
Co-lead board narratives and decks for quarterly meetings.
Cascade executive decisions and strategic direction while channeling organizational feedback upward.
Drive follow-through on executive decisions and commitments.
Design and improve planning, reporting, decision-making, administration, and cross-functional coordination processes.
Own decision-making infrastructure, approval workflows, and vendor/procurement review.
Identify organizational friction and process gaps, redesign workflows, and clarify ownership.
Improve collaboration processes and tooling, including thoughtful AI-tool adoption.
Build scalable systems for planning, reporting, and accountability.

Requirements

What you’ll need

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 annual and quarterly planning processes, 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.
Track record designing and implementing business processes, operating cadences, and decision frameworks.
Financial and operational modeling skills.
Data-driven analysis and business intuition for contracting, budgeting, and strategy decisions.
Ability to influence without authority and build trusted relationships across all levels.
Ability to handle confidential information with discretion.
Entrepreneurial self-starter who delivers results without waiting for direction.
Successful completion of a background check, including employment history and advanced degree verification when applicable.
Preferred: Passion for improving care for Medicaid patients.
Preferred: Healthcare experience in value-based care and/or tech-enabled care delivery.
Preferred: Familiarity with Slack, Jira, Confluence, Asana, HubSpot/Salesforce CRM, Jotform, Google Workspace, and AI tools.

Benefits

Comp & perks

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.
Paid Time Off: 20 vacation days 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.
Professional Development Stipend.
Equal opportunity, supportive, and accessible workplace.