HealthSherpa is hiring a
Chief of Staff

Summary

The job description is for a Chief of Staff role in a fast-growing healthcare startup that helps people enroll in ACA health coverage. The role involves handling projects, partnering with the CEO and executive team on strategic initiatives, running company processes, facilitating communication, attending meetings, analyzing data, preparing reports, drafting presentations, being a trusted advisor to the CEO, managing daily operations of the Office of the CEO, and evaluating all requests for the CEO's time. The role is remote-friendly for candidates based in the US.

Requirements

• 5+ years of experience in finance, consulting, complex program management, or other rigorous roles blending strategy and analysis
• A collaborative mindset that works well with all kinds of personalities across distributed teams
• The ability to distill complex ideas, disparate data, and high-level goals into actionable plans
• Hands-on operational skills and the ability to guide complex projects forward
• Proficiency in Excel/Google Sheets (can perform complex functions) and PowerPoint/Google Slides

Responsibilities

• Handle the oversight and execution of important projects that do not neatly fit within the organizational chart or that fall between departments or leadership responsibilities
• Partner with the CEO and executive team on our strategic initiatives from development through successful execution
• Run company processes such as quarterly/annual planning, investment requests, company all-hands, and company objective-setting
• Facilitate communication among the executive team and the broader company, making sure each function has the information they need to succeed
• Attend meetings and manage follow-ups with the CEO, occasionally being a proxy for the CEO
• Analyze data, prepare reports, and draft presentations for partners, including investors and the Board of the company
• Be a trusted collaborator, advisor, and accountability partner to the CEO and executive team
• Manage the daily operations of the Office of the CEO by evaluating all requests for the CEO's time and working collaboratively with the Executive Assistant to ensure time spent is aligned with the priorities of the organization

Preferred Qualifications

• SQL and Tableau/Mixpanel experience (bonus)
• Multi-sided marketplace experience (bonus)
• Startup experience (bonus)

Benefits

• Remote-first company (US-based remote only)
• Great compensation package at a high-growth, profitable company
• Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents
• HSA/FSA options with corresponding contribution limits
• Monthly grocery stipend and home internet reimbursement
• 401K w/ a match after a grace period
• Life and AD&D coverage
• Disability insurance (Short and Long Term)
• Parental leave
• Four (4) weeks of paid vacation in addition to paid holidays
• Home office budget for remote team members
• Mental health and other wellbeing support programs through a partner network