Head of Benefits & Life Insurance Operations

Location: Chicago, IL or Atlanta, GA

Compensation: Flexible based on experience

About Corgi

Corgi is building the next generation of financial institutions.

We’re rebuilding insurance from the ground up with technology, automation, and a fundamentally different approach to operating financial products. We’re building businesses across insurance and financial services, with the ambition to create institutions that are dramatically faster, more efficient, and more customer-centric than what exists today.

We’re looking for an exceptional operator to lead the operational side of our Employee Benefits and Traditional Life Insurance businesses.

The Role

As the Head of Benefits & Life Insurance Operations , you’ll own the operational infrastructure behind Corgi’s employee benefits and traditional life insurance products.

This is a highly cross-functional role. You’ll work across underwriting, sales, product, finance, compliance, carriers, brokers, and technology to make sure these businesses actually work end-to-end— from quoting and enrollment through policy issuance, administration, billing, servicing, and claims.

You’ll be responsible not just for running existing processes, but for figuring out what the processes should be in the first place. This is a role for someone who sees a messy operational problem and immediately wants to understand every step, identify what is broken, and build a better system.

What You’ll Do

• Own operations end-to-end for Corgi’s employee benefits and traditional life insurance businesses.
• Build and continuously improve the operational workflows supporting quoting, applications, underwriting, enrollment, policy issuance, billing, renewals, servicing, and claims.
• Work directly with insurance carriers, reinsurers, TPAs, brokers, administrators, and other external partners.
• Build the operating infrastructure required to launch new insurance products and programs.
• Identify manual, fragmented, or inefficient processes and replace them with scalable systems and automation.
• Partner closely with engineering and product to turn operational workflows into software.
• Establish operational controls, SLAs, quality standards, and reporting.
• Own escalations and solve difficult cases that fall between traditional organizational silos.
• Develop processes for managing eligibility, enrollment, policy changes, beneficiary updates, billing issues, and other policy administration needs.
• Work with underwriting and actuarial teams to ensure operational processes accurately reflect product and risk requirements.
• Partner with compliance and legal to ensure operational workflows meet regulatory and contractual requirements.
• Build relationships with carrier and distribution partners and become a trusted operational counterpart.
• Analyze operational data to identify bottlenecks, failure points, and opportunities for improvement.
• Build the team, systems, and organizational structure needed as the business scales.
• Eventually manage a team responsible for day-to-day benefits and life insurance operations.

What We’re Looking For

• 7+ years of experience in insurance operations, employee benefits, life insurance, brokerage, underwriting operations, policy administration, or a closely related field.
• Deep familiarity with the operational mechanics of insurance.
• Experience working with carriers, brokers, TPAs, reinsurers, or other insurance counterparties.
• A track record of building or rebuilding operational processes.
• Strong analytical and problem-solving skills.
• Exceptional attention to detail.
• The ability to understand complicated processes quickly and simplify them.
• Experience working cross-functionally with product, engineering, finance, compliance, and sales.
• Strong written and verbal communication.
• A high degree of ownership— you should naturally take responsibility for problems rather than wait for someone else to solve them.
• Comfort operating in an environment where the answer often does not already exist.

You’ll Be Especially Good at Corgi If You…

• Are genuinely curious about how insurance businesses work under the hood.
• Enjoy reading policy documents, contracts, filings, and operating procedures.
• Can go deep into a process and understand every exception and edge case.
• Are equally comfortable discussing an insurance workflow with an underwriter and an API with an engineer.
• Default to asking “Why is this done this way?”
• Like building things from scratch.
• Have unusually high standards for operational quality.
• Get excited about eliminating unnecessary manual work.
• Can operate independently without a lot of structure or direction.
• Want to build something significantly bigger than your current job.

Why Corgi

Most insurance companies are built around layers of people, systems, and processes that have accumulated over decades.

We’re starting from scratch. That means you’ll have the opportunity to rethink how insurance operations actually work, and then work with the people building our technology to make that new model real. You won’t simply be maintaining an existing operation. You’ll be designing the operating system for an entirely new insurance business. If you’re an insurance operator who is frustrated by how slowly the industry moves and wants to build something radically better, we’d love to meet you.