VP, Specialty Underwriting

Job Description

Location: Chicago, IL, flexible within the United States

Type: Full-Time

Compensation: $140,000 - $275,000, flexible based on experience

About Corgi

Corgi is building the next generation of financial institutions. We’re rethinking how insurance, financial products, and other complex financial services are built and operated from the ground up.

We move quickly, work across disciplines, and expect people to take meaningful ownership from day one. Our teams are small, ambitious, and highly execution-oriented.

The Role

We’re looking for a Specialty Underwriter to help grow and manage Corgi’s specialty insurance business. You’ll evaluate risks, assess submissions, develop underwriting strategies, and work across teams to build profitable, sustainable insurance products.

This is an opportunity for an underwriting professional who combines strong technical judgment with a practical, commercially minded approach. You’ll have meaningful ownership over underwriting decisions and the opportunity to help shape our approach as the business grows.

What You’ll Do

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• Evaluate insurance submissions, assess risk exposures, and make informed underwriting decisions.
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• Analyze applications, loss histories, financial information, and other relevant risk factors to determine appropriate terms and pricing.
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• Develop and maintain underwriting guidelines, processes, and standards.
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• Work with brokers, agents, and other distribution partners to evaluate opportunities and build strong relationships.
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• Collaborate with actuarial, product, claims, and operations teams to improve underwriting performance and product offerings.
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• Monitor portfolio performance, loss trends, and emerging risks to inform underwriting decisions.
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• Identify opportunities to improve underwriting workflows, processes, and systems.
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• Help build and scale Corgi’s specialty underwriting capabilities as the company expands.
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What We’re Looking For

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• Experience in commercial or specialty insurance underwriting, 3-8 years of experience.
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• Strong analytical skills and sound judgment in evaluating complex or nonstandard risks.
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• Understanding of underwriting principles, pricing considerations, policy terms, and risk selection.
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• Strong communication and relationship-building skills.
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• A detail-oriented, commercially minded approach to evaluating risk and making decisions.
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• Ability to take ownership, work independently, and adapt in a fast-paced environment.
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Nice to Have

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• Experience across one or more property and casualty insurance lines.
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• Experience working with brokers, agents, or other distribution partners.
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• Familiarity with underwriting systems, data analysis, and process automation.
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• Experience helping develop underwriting guidelines or launch new insurance products.
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Why Corgi

At Corgi, you’ll have the opportunity to help shape a growing insurance business, take meaningful ownership of underwriting decisions, and work closely with a team that is rethinking how insurance is built and operated. You’ll have the flexibility to improve existing processes, explore new opportunities, and contribute directly to the development of our specialty insurance portfolio.

Compensation & Benefits

Compensation will be competitive and based on experience, qualifications, and work location. Corgi offers health insurance and other benefits in accordance with company policies.

Equal Employment Opportunity: Corgi is an equal opportunity employer. We are committed to providing equal employment opportunities to all employees and applicants and do not discriminate on the basis of any characteristic protected by applicable federal, state, or local law. We welcome applicants from all backgrounds and are committed to maintaining an inclusive workplace.