Vice President of Insurance Transformation

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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.

What you’ll do

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, schedule confidence, and trade-off options.
• Translate delivery realities into business and financial terms, enabling informed decisions on scope, investment, and sequencing.
• Prepare and present Board-level updates on Apex progress, expansion milestones, and strategic commitments — with the clarity and credibility that comes from being close to the execution.
• Manage and communicate status that isn't grounded in execution reality.

Within the first year, a successful VP of Insurance Transformation will have:

• Established clear ownership and accountability across all business workstreams contributing to Apex.
• Materially reduced BRD/PRD cycle times and eliminated chronic late-discovery patterns that stall engineering.
• Delivered a formalized, Board-aligned multi-year capability roadmap with defined state expansion criteria and sequencing.
• Enabled a Q2 planning cycle and beyond where business readiness is a strength, not a constraint.
• Built a functioning, high-trust operating model between the business and IT delivery organizations.
• Positioned Hagerty to scale E+ to additional states with confidence in product performance, operational readiness, and financial sustainability.

This might describe you

You are a seasoned insurance transformation leader who has been in the weeds of a major platform implementation and knows exactly where business-side accountability breaks down — and how to fix it. You are as comfortable in a SteerCo presenting to the Board as you are in a working session untangling a requirements dependency with a module owner. You don't wait for IT to surface business problems. You don't accept "we're working on it" as a status. You build operating discipline around you, hold your peers to commitments, and create the conditions for your engineering partners to move fast.

Required

• 12+ years of progressive leadership experience in insurance, with deep familiarity with policy administration, billing, claims, and distribution.
• Demonstrated experience leading or co-leading large-scale core insurance platform transformations (Duck Creek, Guidewire, Majesco, or equivalent).
• Proven ability to drive cross-functional business alignment in complex, matrixed environments — across product, actuarial, compliance, operations, and distribution.
• Track record of owning and improving business requirements processes in transformation programs — not just overseeing them.
• Experience defining state expansion strategy and managing regulatory readiness in multi-state P&C environments.
• Exceptional executive communication skills — able to translate program complexity into clear, decision-enabling narratives for the C-suite and Board.
• Comfortable operating with urgency, making trade-off decisions with incomplete information, and holding others accountable when commitments slip.

Preferred

• Experience in specialty or enthusiast insurance segments.
• Familiarity with agile and hybrid delivery models in enterprise transformation contexts.
• Prior experience working alongside or managing a PMO/APMO function.
• Background in building or restructuring program governance models during active transformation.

Other things to note

• This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart.  

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. 

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If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!