Chief of Staff, Business Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of Waymark’s strategic planning framework, which encompasses multi-year vision, company objectives, resource allocation, annual and quarterly planning, as well as department roadmap integrations.

• Lead the OKR/goal-setting initiative, which includes defining objectives, consolidating results, monitoring progress, and implementing corrective actions.

• Manage the executive operational rhythm, coordinating leadership meetings, tracking decisions, conducting quarterly business reviews, and organizing executive offsites.

• Provide the executive team with analyses of company performance, potential risks, trade-offs, and strategic recommendations.

• Direct high-priority cross-functional projects and navigate ambiguous special initiatives.

• Oversee the internal communications strategy and its scheduling.

• Organize and produce all-company meetings, leadership communications, and corporate events.

• Compose and refine executive communications, strategy narratives, decision memos, and presentation materials.

• Co-manage board narratives and presentations for quarterly meetings.

• Relay executive decisions and strategic guidance while facilitating upward feedback from the organization.

• Ensure follow-through on executive decisions and commitments.

• Design and enhance processes for planning, reporting, decision-making, administration, and cross-functional collaboration.

• Manage the decision-making infrastructure, including approval workflows and vendor/procurement assessments.

• Identify areas of organizational friction and process shortcomings, redesign workflows, and clarify ownership responsibilities.

• Enhance collaboration processes and tools, including the thoughtful integration of AI tools.

• Develop scalable systems for planning, reporting, and accountability.

⛳️ Requirements

• Over 7 years of experience in business operations, chief of staff roles, strategy, or consulting, specifically within the healthcare sector.

• Proven success operating at the executive level in a dynamic, high-growth setting.

• Advanced proficiency in PowerPoint deck creation and Excel modeling.

• Practical experience in designing and executing company-wide annual and quarterly planning processes, OKRs or equivalent goal frameworks, and performance management rhythms.

• Outstanding written and verbal communication skills, including executive memos, presentations, and company-wide communications.

• Ability to simplify complex concepts into concise narratives for executive and all-employee audiences.

• Proven track record in designing and implementing business processes, operational rhythms, and decision-making frameworks.

• Skills in financial and operational modeling.

• Data-driven analytical skills and business acumen for contracting, budgeting, and strategic decisions.

• Ability to influence without direct authority and cultivate trusted relationships across all levels.

• Capability to handle confidential information with care.

• Self-motivated entrepreneur who produces results proactively.

• Successful completion of a background check, including verification of employment history and advanced degree, when applicable.

• Preferred: A passion for enhancing care for Medicaid patients.

• Preferred: Experience in healthcare related to value-based care and/or technology-enabled care delivery.

• Preferred: Familiarity with tools such as Slack, Jira, Confluence, Asana, HubSpot/Salesforce CRM, Jotform, Google Workspace, and AI technologies.

🏝️ Benefits

• Stock Options: Opportunity to invest in the company’s growth.

• Work-from-Home Stipend: A dedicated stipend for your first year to assist in setting up your home office.

• Medical, Vision, and Dental Coverage: Comprehensive plans to ensure you and your family’s health.

• Life Insurance: Basic life insurance coverage.

• 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.