Chief of Staff

Location: Berkeley / San Francisco Bay Area (Hybrid)
Type: Full-Time
Reports to: CEO (Amrish Singh, Co-Founder & CEO)

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.

• 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

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.

• 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
  

• 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

• 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