Director, Claims Learning & Capability

Gallagher•Rolling Meadows, IL

6d•Remote

About The Position

The Director, Claims Learning & Capability is responsible for leading the strategy, design, and execution of learning across the claims organization. This role ensures that new hires and tenured adjusters build the technical expertise, judgment, and operational excellence required to deliver consistent, high-quality outcomes for our clients. Leading a team of liability and workers’ compensation technical training managers, this role oversees onboarding at scale (approximately 55 hires per month), ongoing capability development, and the evolution of learning programs that align with business priorities, regulatory expectations, and emerging industry trends.

Requirements

8–12+ years of experience in claims, learning & development, or workforce capability roles
Demonstrated experience leading teams, preferably managing leaders
Strong understanding of claims operations (Workers’ Compensation and/or Liability preferred)
Experience designing and scaling onboarding and development programs in a high-growth or high-volume environment
Proven ability to influence senior leaders and operate as a strategic partner to the business
Strong operational mindset with the ability to balance strategy and execution
Experience leveraging technology and data to enhance learning outcomes

Responsibilities

Define and execute a comprehensive claims learning strategy aligned to operational goals and client expectations
Evolve learning from “training delivery” to capability building, with a focus on performance outcomes
Partner with Claims leadership to identify skill gaps and translate them into targeted development solutions
Integrate technical, behavioral, and decision-making skills across the adjuster lifecycle
Oversee end-to-end onboarding programs, including high-volume new hire intake
Ensure new hires achieve readiness milestones in quality, compliance, and file handling expectations
Continuously refine onboarding experience to improve retention, speed to proficiency, and engagement
Design and deliver programs that support adjuster growth beyond onboarding, including intermediate and advanced skill development
Embed continuous learning into day-to-day operations through tools, resources, and manager enablement
Partner with Operations to align training with real-time business needs, including workload shifts and emerging risks
Lead and develop a team of Claims Technical Training Managers responsible for program delivery
Establish clear performance expectations, coaching rhythms, and development plans across the team
Drive consistency, scalability, and operational excellence in learning delivery
Ensure alignment across regions, jurisdictions, and client segments
Collaborate with Claims Operations, HR, Strategic Initiatives, WOOEM, Quality, Compliance, Technology teams, and more to ensure learning is integrated into broader business initiatives
Partner with technology teams to leverage tools that enhance learning, such as workflow support, knowledge systems, and AI-enabled solutions
Support client conversations where learning and capability are part of the value proposition
Establish metrics to evaluate learning effectiveness (e.g., time to proficiency, quality outcomes, retention, and engagement)
Use data and insights to continuously improve programs and demonstrate business impact
Build reporting and feedback loops with leadership and frontline managers

Benefits

Medical/dental/vision plans, which start from day one!
Life and accident insurance
401(K) and Roth options
Tax-advantaged accounts (HSA, FSA)
Educational expense reimbursement
Paid parental leave
Digital mental health services (Talkspace)
Flexible work hours (availability varies by office and job function)
Training programs
Gallagher Thrive program – elevating your health through challenges, workshops and digital fitness programs for your overall wellbeing
Charitable matching gift program