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Insurtech Chicago Jobs (NOW HIRING)

Liberate

Enterprise Account Executive

San Francisco, CA · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Chicago, IL · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Atlanta, GA · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Columbus, OH · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Dallas, TX · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

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Insurtech Chicago information

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$10

$67

$125

How much do insurtech chicago jobs pay per hour?

As of Jun 10, 2026, the average hourly pay for insurtech chicago in the United States is $67.68, according to ZipRecruiter salary data. Most workers in this role earn between $23.32 and $92.31 per hour, depending on experience, location, and employer.

What types of projects do professionals typically work on in Insurtech roles based in Chicago?

In Insurtech roles in Chicago, professionals often collaborate on innovative projects such as developing digital insurance platforms, implementing data analytics for risk assessment, and creating customer-centric mobile applications. Teams are usually cross-functional, bringing together software developers, data scientists, product managers, and insurance experts to address industry challenges. The dynamic environment encourages continuous learning and adaptation to new technologies, offering plenty of opportunities for professional growth and advancement within both startups and established insurance companies.

What are the key skills and qualifications needed to thrive in an Insurtech role in Chicago, and why are they important?

To thrive in an Insurtech role in Chicago, you need a solid understanding of insurance fundamentals, data analytics, and technology integration, often backed by a degree in business, finance, or computer science. Familiarity with insurtech platforms, digital claims processing systems, and data analysis tools like SQL or Python is typically required. Strong problem-solving, adaptability, and communication skills help professionals navigate a rapidly evolving industry and collaborate with cross-functional teams. These competencies are crucial for driving innovation and efficiency in Chicago’s competitive insurance technology market.

What is Insurtech Chicago?

Insurtech Chicago refers to the community and ecosystem of insurance technology (insurtech) companies, startups, investors, and professionals based in Chicago. This group focuses on leveraging technology to innovate and improve the insurance industry, from customer experience to underwriting and claims management. Insurtech Chicago often hosts networking events, conferences, and educational sessions to connect industry leaders and foster collaboration. The city is becoming a hub for insurtech due to its strong financial sector, talent pool, and supportive business environment.

What is the difference between Insurtech Chicago vs Insurance Underwriter?

AspectInsurtech ChicagoInsurance Underwriter
CredentialsTypically requires a bachelor’s degree in business, finance, or related fieldsRequires a bachelor’s degree; certifications like CPCU or ARM are common
Work EnvironmentTech-driven startups, insurance technology companies, innovation hubsInsurance companies, underwriting departments, corporate offices
Industry UsageFocuses on insurance technology solutions, digital platforms, and innovationFocuses on evaluating risks, pricing policies, and approving coverage

Insurtech Chicago involves working within technology-focused insurance companies or startups, emphasizing innovation and digital solutions. In contrast, Insurance Underwriters primarily assess risks and determine policy terms within traditional insurance firms. Both roles require similar educational backgrounds and industry knowledge but differ in work environment and focus areas.

What cities are hiring for Insurtech Chicago jobs? Cities with the most Insurtech Chicago job openings:
What states have the most Insurtech Chicago jobs? States with the most job openings for Insurtech Chicago jobs include:
What job categories do people searching Insurtech Chicago jobs look for? The top searched job categories for Insurtech Chicago jobs are:
Insurtech Chicago jobs near you
Infographic showing various Insurtech Chicago job openings in the United States as of June 2026, with employment types broken down into 100% Full Time. Highlights an 50% In-person, and 50% Remote job distribution, with an average salary of $140,766 per year, or $67.7 per hour.

Enterprise Account Executive

Liberate

San Francisco, CA • On-site

$140K - $175K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 3 days ago

Job description

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. We've raised $72M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.
Role OverviewWe 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.
Qualifications
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).
Benefits:
  • 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

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