Chief of Staff

Job Summary

To support a growing health insurance start-up, the full-time remote Chief of Staff will drive execution on critical cross-functional initiatives, manage executive communications, and champion AI adoption across the organization.

Key responsibilities

• Drive high-priority cross-functional initiatives and facilitate strategic planning with the executive team
• Prepare compelling materials for Board meetings and investor relations, including executive updates and strategic memos
• Champion AI adoption by identifying use cases and building workflows to enhance operational efficiency

Required qualifications

• 4-7+ years of operating experience in high-growth start-ups, consulting, or similar environments
• Strong analytical skills with a comfort in financial models and KPI dashboards
• Exceptional written and visual communication skills for executive-level materials
• Deep hands-on AI fluency with experience in structured workflows and automation
• Healthcare experience, particularly in health insurance or related fields, is strongly preferred