Vice President of Insurance Transformation
Hagerty · United States · 2 wk ago
RemoteRemoteBusiness DevelopmentFull-time
What You’ll Do
- 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.
- Drive accountability across all business workstreams, eliminating the upstream bottlenecks that stall engineering teams and erode delivery confidence.
- 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.
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.
- Drive down cycle times on business requirements and decisions; treat slow discovery as a delivery risk, not a process inconvenience.
- Establish and enforce readiness gates that prevent features from entering execution without defined scope, clear decisions, and resolved dependencies.
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.
- Cookordination 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.
- Cookordination across Filings & Compliance, Underwriting, and Operations to ensure state readiness is not a last-minute scramble but a managed, predictable milestone.
- Lead the development of a multi-year state rollout roadmap aligned to Board commitments, with explicit expansion gates and performance checkpoints.
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.
- Maintain clear decision rights and escalation paths so that open decisions are closed quickly and the program is not stalled by ambiguity.
- Resolve cross-functional conflicts, competing priorities, and resource contention at the business level — preventing these issues from cascading into IT delays.
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.
- Translate delivery realities into business and financial terms, enabling informed decisions on scope, investment, and sequencing.
What Success Looks Like (First 12 Months)
- 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.
- Built a functioning, high-trust operating model between the business and IT delivery organizations.
- Enabled a Q2 planning cycle and beyond where business readiness is a strength, not a constraint.
- Delivered a formalized, Board-aligned multi-year capability roadmap with defined state expansion criteria and sequencing.
- Materially reduced BRD/PRD cycle times and eliminated chronic late-discovery patterns that stall engineering.
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.
- Exceptional executive communication skills — able to translate program complexity into clear, decision-enabling narratives for the C-suite and Board.
- Experience defining state expansion strategy and managing regulatory readiness in multi-state P&C environments.
- Track record of owning and improving business requirements processes in transformation programs — not just overseeing them.
- Proven ability to drive cross-functional business alignment in complex, matrixed environments — across product, actuarial, compliance, operations, and distribution.
- Demonstrated experience leading or co-leading large-scale core insurance platform transformations (Duck Creek, Guidewire, Majesco, or equivalent).
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.
- Prior experience working alongside or managing a PMO/APMO function.
- Familiarity with agile and hybrid delivery models in enterprise transformation contexts.
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.
- 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 recruiting@hagerty.com 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.
- EEO/AA US Benefits Overview Canada Benefits Overview UK Benefits Overview
- 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.
- 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.
- 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 recruiting@hagerty.com for compensation, comprehensive benefits and the perks that set us apart.
- Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable.
- 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.