VP, Operations

About Corgi Transportation

Corgi Transportation provides insurance for trucking and business auto through a network of retail brokers, wholesalers, and MGAs. We are building a business where strong underwriting, proprietary technology, and exceptional service work together to make insurance faster and easier for our partners and insureds.

The Role

We are hiring a Vice President of Operations to own the operational execution of Corgi Transportation and build the infrastructure to support our next stage of growth. You will turn business priorities into clear processes, accountable teams, and measurable results across policy administration, partner onboarding, servicing, and operational controls.

This is a hands-on executive role. You should be comfortable setting the operating plan, hiring leaders, investigating a policy issue, and working with engineers to fix the process that caused it. You will partner closely with the Co-CEOs and leaders across Underwriting, Engineering, Sales, Finance, Compliance, and Claims.

What You Will Own

• Daily operations. Lead the workflows supporting submissions, binding, policy issuance, endorsements, renewals, cancellations, and reinstatements. Establish clear ownership, service standards, escalation paths, and quality checks across the policy lifecycle.
• Partner and insured experience. Build reliable onboarding and servicing for MGAs, wholesalers, and retail brokers. Resolve complex operational escalations, improve communication, and eliminate recurring friction.
• Team and capacity. Hire, develop, and manage the operations team. Establish training, performance expectations, staffing plans, and operating budgets that support growth while improving productivity and cost to serve.
• Systems and automation. Translate operational needs into requirements for Engineering. Prioritize improvements based on business impact, lead user testing and rollout, and ensure system migrations and product launches are operationally ready.
• Controls and financial accuracy. Work with Finance and Compliance to maintain accurate policy data, billing, premium collection, commissions, refunds, and required filings. Build documented procedures, reconciliation workflows, and audit trails; investigate and resolve exceptions.
• Performance and execution. Create dashboards and a weekly operating cadence covering turnaround times, backlogs, errors, service levels, productivity, and costs. Identify root causes, assign corrective actions, and follow through until problems are resolved.

What You Bring

• Significant experience leading operations at a property and casualty insurer, MGA, or insurance technology company, with a record of building and scaling teams.
• Strong knowledge of commercial insurance operations and the connections between underwriting, distribution, policy administration, billing, and compliance. Commercial auto or trucking experience is strongly preferred.
• Demonstrated success improving service levels, reducing errors, and increasing capacity through better processes and technology.
• Experience implementing or improving policy administration systems and working directly with technical teams.
• Strong analytical and financial judgment, including the ability to manage budgets, forecast staffing needs, and evaluate operational tradeoffs.
• Clear communication, sound judgment under pressure, and a willingness to take ownership of difficult problems across departmental boundaries.

What Success Looks Like

Partners receive fast, accurate, and predictable service. Teams know what they own and are accountable for results. Leaders can see performance and emerging problems in reliable data. New products and distribution relationships launch with the systems and processes they need. The business handles more volume with fewer errors and less manual work per policy.

Why Join

You will work directly with the Co-CEOs and have the opportunity to shape how Corgi Transportation operates as it grows. The decisions you make about people, systems, and execution will directly influence our ability to serve partners, support underwriting discipline, and build a durable insurance business.

The pay range is representative of on-target earnings (OTE).