VP of Operations

Flexible Compensation and Equity Options

Locations: San Francisco, CA, Chicago, IL, and London, UK

About Corgi

Corgi is a full-stack insurance carrier building better, faster insurance products from the ground up. We're not just a broker: we design, underwrite, price, and issue policies directly, with fewer handoffs and less friction. Insurance is the largest unautomated industry in financial services, and we're rebuilding it using AI. We've raised $374M from Kindred, TCV, and others to do so. YC S24.

The Role

We are looking for a VP of Operations to build and lead the systems that make Corgi run. This is a hands-on leadership role for someone who enjoys creating order from complexity, scaling processes, and driving execution across a fast-moving business.

You will own operational strategy and execution across the company— ensuring teams, workflows, vendors, and core business operations function efficiently and scale alongside our growth. This role sits at the center of the organization and partners closely with leadership across insurance operations, finance, legal, people, and product.

We're not looking for someone who wants to manage from a distance. We want someone who can move between strategy and execution seamlessly— designing systems, solving problems, and helping the company operate at a high level every day.

What You'll Do

• Own and improve company-wide operational systems and processes.
• Build scalable workflows and operating infrastructure across teams and entities.
• Drive cross-functional execution and ensure priorities move quickly and effectively.
• Identify operational bottlenecks and implement practical solutions.
• Develop and monitor KPIs, reporting, and operational performance metrics.
• Manage and improve vendor, partner, and operational relationships.
• Support organizational planning, resourcing, and execution against company goals.
• Partner closely with Finance, Insurance Operations, Legal, and leadership on strategic initiatives.
• Build and lead high-performing operational teams over time.
• Establish strong internal controls, documentation, and operating discipline as the company scales.
• Own special projects and company-building initiatives that don't fit neatly into a single department.

What We're Looking For

• 5–10+ years of experience in operations, business management, consulting, or related leadership roles.
• Experience building systems and processes in high-growth or complex environments
• Strong operator mindset, you enjoy making organizations run better.
• Excellent judgment and ability to navigate ambiguity.
• Highly organized with strong attention to detail and follow-through.
• Comfortable working across functions and influencing without bureaucracy.
• Analytical and data-driven, with strong problem-solving skills.
• Low ego and highly execution-oriented.
• Comfortable owning both strategic decisions and day-to-day execution.

Nice to Have

• Experience in insurance, financial services, fintech, or regulated industries.
• Experience managing multi-entity or operationally complex businesses.
• Experience leading teams and building operational functions from the ground up.