VP, Insurance Technology

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 an Insurance Technology Lead to help shape how our insurance products and internal systems are built. This is a hands-on product role for someone who enjoys working at the intersection of insurance, technology, and operations.

You’ll work closely with engineering, underwriting, and operations to identify opportunities, translate business needs into product requirements, and drive projects from initial idea through launch. You’ll have significant ownership over what gets built and how it works, with the opportunity to make a direct impact on how Corgi develops and scales its insurance business.

This role is ideal for a product-minded operator who understands complex workflows, enjoys solving practical problems, and wants more responsibility than a traditional product management role might offer at a larger company.

What You’ll Do

• Own product development: Identify opportunities to improve our insurance products, systems, and workflows, taking initiatives from discovery and prioritization through implementation and launch.
• Translate business needs into technology: Work with underwriting, operations, and other teams to understand existing processes and turn them into clear product requirements, specifications, and actionable engineering tasks.
• Partner with engineering: Collaborate closely with engineers to design solutions, make trade-offs, clarify requirements, and ensure the right things get built.
• Improve insurance workflows: Find ways to make insurance processes more efficient, reliable, and scalable through better software, automation, and product design.
• Drive cross-functional projects: Coordinate stakeholders, manage timelines, resolve blockers, and keep projects moving in a fast-paced environment.
• Understand the details: Develop a deep understanding of our insurance products, systems, and operational processes so you can identify problems and propose thoughtful solutions.
• Measure results: Evaluate how new features and process improvements perform, gather feedback, and continuously refine the product.
• Build from first principles: Help establish product processes and best practices as the team grows, without adding unnecessary complexity or bureaucracy.

What We’re Looking For

• 3-8 years of experience in product management, product operations, business operations, technology consulting, or a similarly cross-functional role.
• Strong problem-solving skills and the ability to break down ambiguous business problems into clear, actionable solutions.
• Excellent communication skills and the ability to work effectively with both technical and nontechnical teams.
• A high degree of ownership, organization, and follow-through.
• Comfort working in a fast-moving environment where priorities can change and you may need to figure things out as you go.
• Genuine interest in how software can improve complex business processes.

Nice to Have

• Experience in insurance, financial services, InsurTech, or another complex, regulated industry.
• Experience working directly with software engineers on product development.
• Familiarity with APIs, data workflows, automation, or internal business systems.
• Experience taking a product, feature, or operational initiative from concept to launch.

Why Corgi

At Corgi, you’ll have the opportunity to take meaningful ownership early, work directly with decision-makers, and help build technology that supports a growing insurance business. Rather than owning a narrow piece of a mature product, you’ll help identify what needs to be built, work across teams to make it happen, and see the results of your work firsthand.

We’re looking for someone who is curious, resourceful, and excited to build—not someone who needs a large team or established processes to be effective.

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.