Learning Development Operations Jobs in Chicago, IL

The Director of Learning & Capability is responsible for leading the strategy, design, and execution of learning across the GB Operations. This role ensures that new hires and tenured employees are provided with tools, resources, and support to build the technical expertise, judgment, and operational excellence required to deliver consistent, high-quality outcomes for our clients. 

Leading a team of line of business specific and specialized technical training managers, this role oversees technical onboarding at scale , ongoing operational capability development, and the evolution of learning programs that align with business priorities, regulatory expectations, and emerging industry trends. 

Learning Strategy & Capability Development 

• 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 GB leadership to identify skill gaps and translate them into targeted development solutions 

• Integrate technical, behavioral, and decision-making skills across the claim/program lifecycle 

Onboarding & Talent Development 

• Oversee end-to-end onboarding programs, including high-volume new hire intake  

• Ensure new hires achieve readiness milestones in quality, compliance,  file handling expectations, and leadership, where applicable 

• Continuously refine onboarding experience to improve retention, speed to proficiency, and engagement 

Ongoing Development & Performance Enablement 

• 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 

• Deveop a state-of-the-art customer service certification experience 

Team Leadership & Operations 

• Lead and develop a team of 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, coverage types, and client segments 

Cross-Functional Partnership 

• Collaborate with Claims Operations, HR, Strategic Initiatives, WOOEM, Quality, Compliance, Marketing, Internal Communications, Technology teams, and others 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 engagements where learning and capability are part of the value proposition 

Measurement & Continuous Improvement 

• 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 

Required Skills: 

• 8+ years of experience in claims or the risk and insurance industry 

• 2+ years of experience in learning & development, or workforce capability roles  

• Demonstrated experience leading teams, preferably managing leaders  

• Strong understanding of 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  

• Proficient in the Microsoft suite of solutions with a focus on SharePoint, TEAMS, Viva Engage, Power Automate 

• Strong operational mindset with the ability to balance strategy and execution  

• Experience leveraging technology and data to enhance learning outcomes 

• Familiarity with an LMS and the tools used to develop the content within (Articulate, Camtasia, Canva, etc.). 

Travel: Less than 10% 

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We offer a competitive and comprehensive compensation package. The base salary range represents the anticipated low end and high end of the range for this position. The actual compensation will be influenced by a wide range of factors including, but not limited to previous experience, education, pay market/geography, complexity or scope, specialized skill set, lines of business/practice area, supply/demand, and scheduled hours. On top of a competitive salary, great teams and exciting career opportunities, we also offer a wide range of benefits. 

Below are the minimum core benefits you’ll get, depending on your job level these benefits may improve:

• 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

Other benefits include:

• 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
• And more...

**The benefits summary above applies to fulltime positions. If you are not applying for a fulltime position, details about benefits will be provided during the selection process.

We value inclusion and diversity

Click Here to review our U.S. Eligibility Requirements

Inclusion and diversity (I&D) is a core part of our business, and it’s embedded into the fabric of our organization. For more than 95 years, Gallagher has led with a commitment to sustainability and to support the communities where we live and work.

Gallagher embraces our employees’ diverse identities, experiences and talents, allowing us to better serve our clients and communities. We see inclusion as a conscious commitment and diversity as a vital strength. By embracing diversity in all its forms, we live out The Gallagher Way to its fullest.

Gallagher believes that all persons are entitled to equal employment opportunity and prohibits any form of discrimination by its managers, employees, vendors or customers based on race, color, religion, creed, gender (including pregnancy status), sexual orientation, gender identity (which includes transgender and other gender non-conforming individuals), gender expression, hair expression, marital status, parental status, age, national origin, ancestry, disability, medical condition, genetic information, veteran or military status, citizenship status, or any other characteristic protected (herein referred to as “protected characteristics”) by applicable federal, state, or local laws.

Equal employment opportunity will be extended in all aspects of the employer-employee relationship, including, but not limited to, recruitment, hiring, training, promotion, transfer, demotion, compensation, benefits, layoff, and termination. In addition, Gallagher will make reasonable accommodations to known physical or mental limitations of an otherwise qualified person with a disability, unless the accommodation would impose an undue hardship on the operation of our business.

Required Skills: 

• 8+ years of experience in claims or the risk and insurance industry 

• 2+ years of experience in learning & development, or workforce capability roles  

• Demonstrated experience leading teams, preferably managing leaders  

• Strong understanding of 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  

• Proficient in the Microsoft suite of solutions with a focus on SharePoint, TEAMS, Viva Engage, Power Automate 

• Strong operational mindset with the ability to balance strategy and execution  

• Experience leveraging technology and data to enhance learning outcomes 

• Familiarity with an LMS and the tools used to develop the content within (Articulate, Camtasia, Canva, etc.). 

Travel: Less than 10% 

#LI-JA1

#Remote