Chief of Staff
About the role
Operational leadership role reporting to the CEO to turn chaos into an operating system, drive cross-functional initiatives, and scale the company from within. 18–24 month tour with potential internal leadership path.
Responsibilities
- Be an extension of the CEO across the org — walk into any function (sales, ops, engineering, growth) and drive alignment, remove roadblocks, and push things forward with the same context and urgency
- Build our operating system from scratch — leadership meetings, OKR tracking, quarterly planning
- Own board materials, investor updates, and cap table management end-to-end
- Drive the highest-priority cross-functional initiative at any given time — M&A (target ID, diligence, integration), new vertical expansion, or standing up operational playbooks as we scale
- Turn tribal knowledge into systems — map, document, and build scalable processes
- Plug functional gaps — step into leadership roles as the exec team is assembled
- Fix things that are broken before anyone notices they’re broken
- Install an execution cadence with clear priorities, owners, deadlines, and weekly scoreboards
- Build repeatable runbooks for messy operational workflows and push toward automation (human <> AI handoffs)
- Ensure high-stakes operational surfaces do not degrade (submission quality, underwriting throughput, quoting speed, customer response time)
- Increase CEO leverage by ensuring critical work ships without requiring constant CEO intervention
Qualifications
- 4–7 years of experience in high-intensity environments (banking, consulting, PE, startup ops, or founding)
- Strong financial modeling and analytical skills
- Exceptional written and verbal communication
- Based in San Francisco or willing to relocate immediately
Skills
Benefits
- Health, dental, and vision insurance
- Housing stipend
- Daily meals ($60/day)
- Commuter benefits (Uber covered)
- Team meals and snacks
About Harper
AI-native commercial insurance brokerage
At Harper, we are building a fully autonomous commercial insurance brokerage powered by AI. Our initial focus is on mid-sized businesses with complex insurance needs, but our vision is to eventually serve every business in the country. By leveraging AI to automate key workflows in the insurance process, we efficiently secure optimal coverage for each client's unique requirements at competitive prices and with rapid turnaround. Our AI system learns from the expertise of our brokers, accumulating not just knowledge but also the specific workflows, data, and capabilities that pave the way to full autonomy.
More open roles at Harper
- GTM Engineer7mo agoHybrid (San Francisco) · Engineering
- Special Projects Lead8mo agoSan Francisco · Operations
- Account Manager8mo agoSan Francisco
- Head of Customer Experience8mo agoHybrid (San Francisco) · Harper - CX/Operations
- Recruiting Lead9mo agoHybrid (San Francisco)