Chief of Staff to the CEO
Location: Berkeley / San Francisco Bay Area (Hybrid)
Type: Full-Time
Reports to: CEO (Amrish Singh, Co-Founder & CEO)
About Liberate
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.
Role Overview
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.
What You’ll Do
1) CEO Leverage & Operating Cadence
- 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
2) Strategic Planning & Execution
- 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
3) Cross-Functional Leadership & Business Operations
- 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
4) Data, Metrics, and Insight
- 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
5) Internal & External Communications
- 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
Who You Are
You’re a highly capable operator with strong judgment and elite follow-through. You can shift from strategy to detail seamlessly, communicate clearly, and build trust across teams quickly.
Qualifications (Required)
- MBA from a top school
- 5–10+ years of experience in Communications, 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
Preferred Qualifications
- 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
Why Join Liberate
- Work directly with the CEO and leadership team to shape the company’s strategy and operating model
- Make high-impact contributions across product, customers, partnerships, and growth
- Be part of a mission-driven team modernizing one of the largest industries in the world
- Competitive compensation, equity, and benefits
