Vice President of Insurance Transformation

Responsibilities

• Program Leadership & Business Accountability
• Serve as the senior business owner for the full Apex program, spanning Core platform migration and the Enthusiast+ product buildout across all states.
• Own the business side of the integrated program plan - ensuring that requirements, decisions, approvals, and readiness milestones are delivered on time and at the quality needed to sustain IT execution.
• Drive accountability across all business workstreams, eliminating the upstream bottlenecks that stall engineering teams and erode delivery confidence.
• Partner directly with the IT program leadership and the Principal Project Manager (a direct report) to maintain a single, integrated view of program health, risk, and delivery trajectory.
• Requirements Ownership & Business Readiness
• Own the BRD/PRD pipeline - ensuring business requirements are shaped, prioritized, and ready for planning cycles before capacity is committed.
• Establish and enforce readiness gates that prevent features from entering execution without defined scope, clear decisions, and resolved dependencies.
• Drive down cycle times on business requirements and decisions; treat slow discovery as a delivery risk, not a process inconvenience.
• Ensure module owners, functional SMEs, and product stakeholders are actively engaged, unblocked, and delivering against agreed timelines.
• State Expansion Strategy & Readiness
• Define and own the criteria that govern when Hagerty is ready to expand E+ and Core into new states - balancing regulatory readiness, operational capacity, and product performance.
• Lead the development of a multi-year state rollout roadmap aligned to Board commitments, with explicit expansion gates and performance checkpoints.
• Coordinate across Filings & Compliance, Underwriting, and Operations to ensure state readiness is not a last-minute scramble but a managed, predictable milestone.
• Ensure expansion decisions are grounded in data, not optimism - and that the program is not building long-term complexity faster than it can be operationalized.
• Cross-Functional Alignment & Stakeholder Leadership
• Align and mobilize leaders across Underwriting/Product, Actuarial & Pricing, State Filings & Compliance, Claims & Operations, Distribution (AEA and Direct), and Finance & Reporting around program priorities and delivery commitments.
• Resolve cross-functional conflicts, competing priorities, and resource contention at the business level - preventing these issues from cascading into IT delays.
• Maintain clear decision rights and escalation paths so that open decisions are closed quickly and the program is not stalled by ambiguity.
• Act as the primary business voice in program governance, SteerCo, and executive forums.
• Executive Communication & Board Reporting
• Provide Jeff Briglia and executive leadership with a credible, transparent view of program status - including honest assessments of risk

Benefits

Additional Information

Say hello to Hagerty Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We're proud to be the world's largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world's largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We're committed to Never Stop Driving. Ready to get in the driver's seat? Join us! Hagerty is amid one a meaningful transformation in its history. The Apex program is replacing the company's core insurance infrastructure - policy administration, billing, claims, data & reporting, and distribution. This transformation is occurring while simultaneously launching a new insurance product Enthusiast+. This expanded product offering that extends Hagerty's risk appetite to a new generation of modern performance vehicles. This is a rare opportunity to own the business side of a full-stack insurance transformation at a brand with a deeply loyal customer base, a differentiated market position, and Board-level commitment to getting this right. The VP of Insurance Transformation is the senior business leader accountable for the Apex program. This person owns the business readiness, cross-functional alignment, and strategic decision-making that determines whether the program delivers. They are the counterpart to the IT engineering and delivery organization, and the executive through whom Hagerty's insurance business functions - Underwriting, Actuarial, Filings, Claims, Operations, Distribution, and Finance - are coordinated, held accountable, and mobilized around a shared delivery plan. This role reports directly to the President of Insurance and carries full ownership of the business's ability to execute.

Your Match

How well this role fits your profile.

Company Intel

What employees say

Worked at hagerty? Share your experience