Chief of Staff

Accountabilities:

• • Own company metrics and reporting: Establish and maintain a reliable source of truth for key business metrics, including transaction volume, take rate, collections, clinician retention, time-to-first-session, and credentialing throughput; define methodologies and ensure metrics are consistently understood across leadership, investors, and the board.
  • Run the operating cadence: Establish effective goal-setting, weekly performance reviews, executive meetings, and strategic initiative reviews, ensuring every priority has clear ownership, status, and next steps.
  • Take ownership of executive workstreams: Gradually assume responsibility for board and investor materials, diligence processes, financing support, external counsel coordination, and key vendor relationships, reducing the CEO's ongoing involvement in these areas.
  • Resolve operational bottlenecks: Identify and address constraints across credentialing, payer enrollment, contracting, revenue cycle management, and clinical operations, including temporarily taking ownership of functions where necessary until sustainable leadership is established.
  • Lead high-priority strategic projects: Own complex, time-sensitive initiatives such as new-state expansion, regulatory and corporate structure projects, build-versus-buy decisions, system migrations, and the creation of new operational functions.
  • Drive cross-functional alignment: Work effectively with clinicians, payer representatives, healthcare counsel, engineers, and operational leaders to move initiatives forward despite incomplete information and competing priorities.
  • Establish scalable operating infrastructure: Within the first 90 days, create a documented metrics layer, implement a strong operating cadence, establish clear accountability across strategic initiatives, and take full ownership of at least one major workstream previously handled by executive leadership.

  Requirements:

  • Experience: 4–8 years in a demanding, high-performance environment such as management consulting, investment banking, private equity, venture capital, or operations at a high-growth startup.
  • Ownership mindset: Demonstrated ability to own outcomes rather than simply provide recommendations, with the initiative and judgment to take loosely defined problems through to completion.
  • Analytical ability: Strong quantitative and modeling skills, including the ability to build business models from scratch, interpret data critically, and recognize when assumptions or methodologies may be misleading.
  • Executive communication: Exceptional written communication skills, with experience creating concise presentations, decks, or strategic memos that influence senior decision-makers.
  • Autonomy: Comfortable operating with minimal direction, filling gaps independently, making reasonable assumptions, and communicating decisions clearly.
  • Adaptability: Comfortable working across highly varied domains and collaborating with subject-matter experts including clinicians, payer representatives, healthcare attorneys, engineers, and operators.
  • Low-ego execution: Willing to switch between strategic and highly tactical work depending on business needs, with a practical approach to getting important things done.
  • Preferred experience: Healthcare experience—particularly multi-state provider operations, payer contracting, or Medicaid—is advantageous but not required.
  • Additional experience: Exposure to marketplaces, multi-sided businesses, management services organizations, or an internal Series B+ fundraising process is a plus.

  Benefits:

  • Base salary: $150,000–$200,000 annually.
  • Equity: 0.1%–0.4% equity participation.
  • Fully remote position available across the United States and Canada.
  • Direct access to senior leadership and exposure to virtually every aspect of a rapidly scaling healthcare business.
  • Broad scope and accelerated opportunity to progress into an operating leadership role.
  • Opportunity to work on initiatives with meaningful impact on access to healthcare services.
  • Take-home interview exercise is compensated for the candidate's time.
  • Fast-moving environment with significant autonomy, responsibility, and ownership.
  • Opportunity to work across strategy, operations, finance, compliance, market expansion, and organizational development.