Training Lead - Guidewire

markelcorp; Richmond (VA); Hybrid; USD 88,000 - 110,000; Full time

Benefits offered by this job

Health, dental and vision insurance

401(k) with employer match

Employee Stock Purchase Plan

PTO, holidays and parental leave

Hybrid work arrangement

Job summary

Markel is seeking a Training Lead - Guidewire to drive design, development, and delivery of training across the Guidewire portfolio for the United States and Bermuda. You will ensure employees gain the knowledge and confidence to adopt new Guidewire processes and technologies.

The ideal candidate is an experienced instructional designer and facilitator who creates engaging learning experiences, role-based programs, and performance support materials to drive adoption and proficiency.

Qualifications

• 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.

Responsibilities

• Instructional Design & Curriculum Development: Conduct needs assessments, design curricula, learning paths, job aids, eLearning content, simulations, and performance support materials.
• Training Delivery & Enablement: Deliver instructor-led, virtual, and train-the-trainer programs; facilitate workshops and end-user sessions; validate content with SMEs; manage participation and reporting.
• Readiness & Adoption: Assess readiness, measure training effectiveness via assessments and adoption metrics, provide post-go-live reinforcement and coaching.
• Collaboration & Continuous Improvement: Align training with release objectives; maintain standards and repositories; contribute to lessons learned across Guidewire releases.

Skills

Instructional design

Facilitation

Stakeholder engagement

Adult learning principles

Curriculum development

Change management

Microsoft 365 tools

Education

Bachelor's degree

Tools

Microsoft Teams

SharePoint

PowerPoint

Copilot

Job description

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 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.

Key Responsibilities

Instructional Design & Curriculum Development

• 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.

Training Delivery & Enablement

• 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.

Readiness & Adoption

• 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.

Collaboration & Continuous Improvement

• 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.

Qualifications

• 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.

Preferred Skills

• 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.

#LI-AB

#LI-Hybrid

US Work Authorization

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

Pay information:

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.

Who we are:

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.

We're all about people | We win together | We strive for better

We enjoy the everyday | We think further

What's in it for you:

In keeping with the values of the Markel Style, we strive to support our employees in living their lives to the fullest at home and at work.

We offer competitive benefit programs that help meet our diverse and changing environment as well as support our employees' needs at all stages of life.

• All full‑time employees have the option to select from multiple health, dental and vision insurance plan options and optional life, disability, and AD&D insurance.
• We also offer a 401(k) with employer match contributions, an Employee Stock Purchase Plan, PTO, corporate holidays and floating holidays, parental leave.

Are you ready to play your