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WaymarkWaymarkUnited States

Business Operations & Chief of Staff

Leads company-wide strategic planning, executive operating rhythms, internal communications, and scalable business processes. The role requires 7+ years in business operations, chief of staff, strategy, or consulting, along with healthcare experience and strong analytical and executive communication skills.

124k – 229k/yr
Remote8+ YOEBusiness Operations

About the role

Responsibilities

Strategic Planning & Management

  • Own the company's strategic planning system, including multi-year vision, company-level annual and quarterly planning cycles, department roadmaps, and prioritization decisions.
  • Drive the OKR and goal-setting process end to end, 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 analysis of company performance, risks, trade-offs, and recommendations.
  • Lead high-priority cross-functional initiatives and special projects involving ambiguous, high-stakes business problems.

Company & Internal Communications

  • Own the 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 presentations.
  • Co-lead board narratives and decks for quarterly meetings.
  • Connect executive leadership with the broader organization by cascading decisions and gathering feedback.
  • Drive follow-through on executive decisions and commitments.

Business Process Development

  • Design, implement, and improve 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 reviews.
  • 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.

Requirements

  • 7+ years of experience in business operations, chief of staff, strategy, or consulting roles, with direct healthcare experience.
  • Experience operating at the executive level in a fast-paced, high-growth environment.
  • Expert proficiency with PowerPoint deck creation and Excel modeling.
  • Hands-on experience designing and running company-level annual and quarterly planning, OKR or equivalent goal frameworks, and performance-management rhythms.
  • Exceptional written and verbal communication, including executive memos, decks, and company-wide communications.
  • Experience designing and implementing business processes, operating cadences, and decision frameworks.
  • Financial and operational modeling skills, with the ability to analyze contracting, budgeting, and strategy decisions.
  • Ability to influence without authority, build trusted relationships, handle confidential information discreetly, and deliver results independently.

Nice-to-Haves

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

Compensation & Benefits

  • Hiring range varies by US employee location: $124,000–$229,000 annually.
  • Stock options.
  • Work-from-home stipend for home-office setup.
  • Medical, vision, and dental coverage.

Skills

PowerPointExcelokrsStrategic PlanningFinancial Modelingoperational modelingSlackJiraConfluenceAsanaSalesforceGoogle WorkspaceAI Tools
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