Senior Change Manager – Guidewire Programs (US & Bermuda)

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it.

The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! Markel is seeking a seasoned and strategic change leader to drive adoption, readiness, and sustained value realization across the Guidewire portfolio for the United States and Bermuda. This role leads end-to-end organizational change delivery for PolicyCenter, BillingCenter, ClaimCenter, and all related integrations, ensuring that business teams are prepared, engaged, and equipped to operate effectively in the future state.
The Senior Change Manager will act as a trusted advisor to program executives, product teams, and operational leaders—embedding organizational readiness, adoption strategies, and operational stability into delivery from design through post implementation.

Key Responsibilities

Change Strategy & Leadership

• Develop and execute the enterprise change strategy for the Guidewire portfolio, aligning change outcomes, adoption goals, and readiness milestones with program roadmaps and release plans.
• Serve as the primary change advisor to executive sponsors and program leadership—surfacing risks, influencing decisions, and reinforcing leadership accountability for business adoption.
• Create and maintain a Guidewire Change Playbook that includes stakeholder maps, readiness criteria, cutover and hypercare processes, and structured Lessons Learned frameworks.

Impact Assessment & Stakeholder Engagement

• Lead comprehensive change impact assessments across functions, regions, and leadership tiers.
• Develop stakeholder engagement strategies to ensure alignment, adoption, and shared ownership of change outcomes.

Communications & Engagement

• Design and deliver integrated communication strategies to support all releases—producing audience targeted materials including executive updates, release summaries, FAQs, and status reporting.
• Ensure communications reinforce key messages, expectations, and calls to action for impacted audiences.

Learning, Enablement & Readiness

• Oversee development of role based learning, leveraging modern enablement tools (in-app guidance, digital walkthroughs, analytics) to ensure scalable and continuous learning.
• Ensure training aligns with future state workflows, business processes, and operating models.
• Establish enterprise readiness criteria and facilitate formal readiness reviews, partnering with delivery teams to close gaps prior to deployment.

Deployment, Stabilization & Adoption

• Lead change components of cutover and post go-live activities including communications, hypercare planning, support models, and feedback loops.
• Monitor adoption, proficiency, and stabilization metrics; translate insights into corrective actions and continuous improvement recommendations.

Collaboration & Continuous Improvement

• Partner closely with Product Solutions, Technology, Engineering, Operations, and regional leadership to integrate change management into delivery plans and sequencing.
• Continuously evolve change standards, playbooks, and tools to strengthen organizational change maturity and improve outcomes across Guidewire releases.

Core Competencies

• Deep understanding of insurance market and regulatory concepts (commercial, specialty).
• Advanced analytical and strategic capability, with strong problem solving skills.
• Demonstrated leadership in matrixed, cross functional, and geographically distributed environments.
• Expertise in enterprise change management, digital transformation, and technology adoption.
• Strong customer and user experience orientation.
• Exceptional stakeholder management and influence skills, including executive level presence.

Qualifications

• 10+ years of experience in change management, organizational development, learning, or transformation; insurance industry experience strongly preferred.
• Proven success leading change for large‑scale technology implementations; Guidewire or comparable insurance core platforms highly preferred.
• Experience with multi‑release, highly integrated programs including complex data migration.
• Experience with modern userenablement technologies (e.g., in-app guidance, digital adoption platforms, analytics).
• Prosci or comparabl