Training Lead - Guidewire

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 realise our potential, we can help others reach theirs.

Join us and play your part in something special! Markel is seeking a Training Lead
- Guidewire to lead training design, development, and delivery across the Guidewire portfolio for the United States and Bermuda. This role is responsible for ensuring employees have the knowledge, skills, and confidence needed to successfully adopt new Guidewire processes and technologies. The ideal candidate is an experienced instructional designer and facilitator who can create engaging learning experiences, role-based training programs, and performance support materials that drive adoption and proficiency.

• Conduct training needs assessments and identify role-based learning requirements.
• Design and develop curricula, learning paths, job aids, eLearning content, simulations, and performance support materials.
• Apply adult learning and instructional design principles to create effective learning experiences.
• Ensure training aligns with future-state business processes and ways of working.

• Deliver instructor-led, virtual, and train-the-trainer programs.
• Facilitate workshops and end-user learning sessions.
• Partner with business SMEs to validate content and learning outcomes.
• Manage learner participation, completion tracking, and reporting.

• Assess learner readiness and proficiency.
• Measure training effectiveness through assessments, feedback, and adoption metrics.
• Support post-go-live reinforcement, coaching, and knowledge retention activities.
• Continuously improve training programs based on learner feedback and business outcomes.

• Partner with Change Management, Product, Technology, and Operations teams to align training with release objectives.
• Maintain training standards, templates, and learning repositories.
• Contribute to lessons learned and continuous improvement activities across Guidewire releases.

• Bachelor’s degree or 7+ years of experience in Training, Learning & Development, Instructional Design, Change Management, or Organizational Effectiveness.
• Proven experience designing and delivering training for large-scale technology implementations.
• Strong instructional design experience, including curriculum development, eLearning, job aids, and performance support tools.
• Strong facilitation, presentation, and stakeholder engagement skills.
• Experience applying adult learning principles and instructional design methodologies.
• Proficiency with Microsoft 365 tools, including Teams, SharePoint, PowerPoint, and Copilot.
• Insurance industry and/or Guidewire experience preferred.

• Experience leveraging AI tools (e.g., Microsoft Copilot, ChatGPT) to accelerate instructional design, content creation, training administration, and learning analytics.
• Ability to translate complex business and technology concepts into clear, engaging learning experiences.
• Experience creating role-based learning programs that improve user proficiency and adoption.

• The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors.
• The national average salary range for the Training Lead
  - Guidewire is $88,000 - $110,000 with 25% incentive.

• US Work Authorization required.
• Markel does not provide visa sponsorship for this position, now or in the future.

Markel Group (NYSE – MKL) a fortune 500 company with over 60 offices in 20+ countries, is a holding company for insurance, reinsurance, specialist advisory and investment operations around the world.

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