Chief of Staff

Liberate•San Francisco, CA

1d•Hybrid

About The Position

Liberate builds AI agents to automate manual tasks for the $2.7T insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance carrier and broker operations. To date, we have raised $72M from top-tier venture capital firms, highlighted by a $50M Series B in September. Liberate is hiring a Chief of Staff (CoS) to partner directly with the CEO to drive company-wide execution, operating cadence, strategic planning, and cross-functional alignment. This role is ideal for someone who thrives in a high-growth, ambiguous environment, enjoys being at the center of decisions, and has the ability to convert strategy into action. You will serve as a force multiplier for the CEO—helping Liberate scale intelligently while maintaining focus on the highest-impact initiatives.

Requirements

MBA from a top school
5–10+ years of experience in Product, strategy, business operations, consulting, or high-growth startup leadership roles
Strong executive communication skills (written and verbal)
Demonstrated ability to run cross-functional programs and drive outcomes through influence
Analytical mindset with comfort using data to support decisions
High discretion, integrity, and ability to manage sensitive information

Nice To Haves

Experience in B2B SaaS, enterprise AI, or regulated industries (insurance/fintech/healthcare)
Experience working directly with founders/CEOs at growth-stage companies
Comfortable operating in a fast-paced, evolving environment with minimal structure

Responsibilities

Build and run the CEO’s operating rhythm across leadership meetings, offsites, strategic reviews, board prep, and key internal communications
Create high-quality briefings, meeting notes, and decision memos
Track and drive closure on CEO priorities and commitments across teams
Partner with the CEO and exec team on annual and quarterly planning (OKRs / KPIs / operating plan)
Translate high-level strategy into a clear execution roadmap
Help identify and resolve constraints and execution bottlenecks quickly
Lead special projects across Product, Engineering, Go-to-Market, Partnerships, Customer Success, and Finance
Improve internal processes and systems as the company grows (e.g., metrics dashboards, program management, internal tooling)
Own outcomes across high-priority programs—even when there’s no clear owner
Build dashboards and reporting mechanisms to give leadership clarity on performance
Develop business insight: customer adoption, sales pipeline health, delivery speed, retention/expansion drivers
Support investor updates and board reporting
Support CEO communications: internal updates, narrative, strategic messaging
Help prepare for investor and customer meetings (briefs, talking points, slides)
Represent the CEO internally—ensuring decisions are clearly communicated and executed