Liberate · 3 days ago
Chief of Staff
San Francisco, CA
Full-time
Onsite
Lead/Staff, Director/Executive
5+ years expLiberate is an innovative company building AI agents to automate tasks for the insurance industry. They are seeking a Chief of Staff to partner with the CEO in driving execution, strategic planning, and cross-functional alignment within the organization.
Information TechnologyInsurTechSaaSSoftware
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
Qualification
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
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
Benefits
Competitive compensation
Equity
Benefits
Company
Liberate
Comprehensive AI Platform for Carriers, Agencies and Brokers Liberate enables you to provide human-like conversation that offers 24/7 support and answers 100% of calls with no wait time.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$72MKey Investors
Battery VenturesRedpointEclipse Ventures
2025-10-14Series B· $50M
2024-05-05Series A· $15M
2023-01-05Seed· $7M
Leadership Team
Amrish Singh
Co-founder and CEO
Jason St Pierre
Chief Product Officer and Co-Founder at Liberate
Recent News
2026-01-22
Crunchbase News
2025-12-11
Company data provided by crunchbase