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Sr. Leader / Head of Learning & Development
Portland, MEApril 4th, 2026
Robert Half Executive Search has been exclusively retained to identify a Head of Learning & Development. Are you ready to shape the future of learning for a nationally recognized membership and services organization supporting a 10,000+ employee workforce? This is a high-visibility enterprise leadership role where you will define and execute the learning strategy across a business unit elevating instructional design, modernizing learning experiences, and driving measurable performance outcomes across a multi-state organization.You will lead a distributed L&D function and partner directly with senior leaders across Claims, Underwriting, HR, Compliance, and Operations to build scalable, high-impact learning solutions that strengthen capability, improve service quality, and support enterprise transformation. If you are a strategic learning architect who combines instructional design excellence with operational leadership and business influence, this is a rare opportunity to make a lasting enterprise impact.Key ResponsibilitiesOwn the end-to-end learning strategy across a multi-state workforceLead the design, architecture, and continuous evolution of instructional experiences, ensuring modern, engaging, and performance-driven learning solutionsOversee curriculum strategy, instructional design standards, learning technologies, and content governanceManage and develop a team of supervisors, instructional designers, and learning professionals across on-site and remote environmentsPartner with senior leaders to identify capability gaps and translate business priorities into scalable learning solutionsDrive enterprise learning initiatives and transformation programs that shape long-term workforce capabilityLeverage data, analytics, and LMS insights to measure effectiveness, demonstrate ROI, and continuously improve learning outcomesWhat We’re Looking ForSenior L&D leadership experience in complex, multi-site or enterprise environmentsDeep expertise in instructional design, curriculum architecture, and modern learning methodologiesProven success building scalable learning programs tied to business performanceStrong people leadership, coaching, and team-building capabilitiesExecutive presence with the ability to influence senior stakeholders across functionsExperience within insurance, financial services, or other regulated industries preferredWhy This RoleEnterprise scope. Long-term stability. Visible impact. A rare opportunity to modernize learning at scale within a highly respected national organization. Compensation: Salary + bonus + pension + comprehensive benefits
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