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. We've raised $72M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.
Role Overview
We are seeking a seasoned Enterprise Account Executive with 10+ years of experience selling enterprise software into insurers and large carriers. This role is responsible for driving new business growth, building executive-level relationships, and positioning Liberate as the trusted partner for insurers looking to modernize and innovate.
This is a quota-carrying role with direct access to Liberate’s leadership, product, and customer success teams.
*Location: Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day/week in-office)
Key Responsibilities- Own the full enterprise sales cycle: prospecting, qualification, solution positioning, negotiation, and close.
- Develop and execute a territory/account plan focused on top-tier insurers and carriers.
- Build and maintain C-level relationships across business (Claims, Underwriting, Operations) and technology (CIO, CTO, CDO) functions.
- Collaborate with Solutions Engineering and Product to tailor AI-driven demos and proofs-of-concept.
- Navigate complex procurement processes in insurance enterprises, including RFPs and multi-stakeholder evaluations.
- Achieve and exceed quarterly/annual sales quotas.
- Contribute customer insights to influence Liberate’s product roadmap.
- Represent Liberate at key industry events, conferences, and roundtables.
Must Have
- Enterprise software sales experience with a strong track record of closing $1M+ ARR deals.
- Proven success selling to insurance carriers, MGAs, or large brokerages.
- Deep understanding of insurance technology ecosystems (policy admin, claims, billing, digital engagement).
- Strong network of relationships in the P&C insurance market.
- Extreme sense of ownership, urgency, and customer obsession, thriving in a Series-A startup environment.
- Excellent storytelling, executive presence, and negotiation skills.
- Ability to collaborate cross-functionally with product, engineering, and customer success.
Nice to Have
- Experience selling AI/ML, automation, or cloud-based platforms.
- Background at high-growth startups.
- Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco).
- Competitive salary with performance-based commissions and equity options
- Flexible PTO
- 401(k) plan
- Comprehensive health, dental, and vision insurance
- Flexible work environment with remote work options
- Collaborative and innovative company culture
Salary Information: $140,000 to $175,000 base salary (depending on experience and location), plus stock and benefits
Top Skills
Similar Jobs
.png)
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
