Head of Learning & Enablement
About The Position
The Head of Learning and Enablement is responsible for building and leading the learning and enablement function at Continental General. This role owns the full lifecycle of learning - from designing and developing training content to delivering it - while also architecting the broader ecosystem in which learning happens: tools, standards, governance, content models, and cultural practices. This is a greenfield role; you will evaluate, select, and implement the platforms and tools needed to support scalable training delivery across the organization. Continental General operates as both an insurance carrier and a Third-Party Administrator (TPA). This role ensures that critical knowledge - spanning insurance products, TPA operations, systems, and emerging tools such as AI - is captured, discoverable, current, and embedded into the way the organization works. The Head of Learning and Enablement enables continuous learning, accelerates onboarding, and drives operational excellence.
Requirements
- Bachelor’s degree required; advanced degree preferred; or the equivalent years of education and experience required.
- Minimum 8 years of experience in the insurance or financial services industry with direct exposure to insurance products such as Term Life, Permanent Life, Annuities, Long-Term Care, and/or Final Expense.
- Experience within a TPA environment is strongly preferred.
- Demonstrated experience designing and delivering enterprise training, learning programs, or enablement solutions - not solely in an advisory or design-only capacity.
- Strong systems thinking skills with the ability to design scalable, sustainable frameworks rather than one off training solutions.
Nice To Haves
- Experience with adult learning principles, instructional design, product training or learning experience design.
- Experience supporting technology adoption, including AI tools, automation, or digital transformation initiatives.
- Familiarity with insurance administration platforms and TPA operational workflows.
- Comfort working cross functionally with leaders, SMEs, and transformation teams.
- Excellent written communication skills, with an emphasis on clarity, usability, and audience first design.
Responsibilities
- Partner with subject matter experts, business leaders, and functional teams to ensure training content is accurate, current, and aligned to strategic priorities.
- Lead training efforts for new tool rollouts, process changes, and technology adoption (including AI and automation initiatives).
- Own end-to-end training delivery - from needs analysis and instructional design through facilitation and post-training reinforcement.
- Design, develop, and deliver training programs covering insurance products (life, annuity, long-term care), TPA operations, systems and tools, AI adoption, and compliance requirements.
- Design and evolve a cohesive learning ecosystem that integrates formal training, informal learning, documentation, communities of practice, and performance support.
- Identify critical capability gaps and ensure learning solutions are aligned to strategic priorities.
- Establish and champion a proactive knowledge management approach that prioritizes product and operational training so that Continental General can brilliantly serve its clients.
- Ensure knowledge artifacts remain current, relevant, and easy to discover across platforms.
- Support transformation initiatives by ensuring people have the right knowledge and tools at the right time to adopt new processes, products, and ways of working.
- Embed learning and knowledge practices into operational rhythms (e.g., onboarding, role changes, process updates, new product launches, tool rollouts).
- Act as a thought partner to the Innovation and Optimization team on how learning enables execution, scalability, and resilience.
- Establish meaningful measures of learning effectiveness and organizational capacity growth (beyond completion metrics).
- Continuously assess and refine the learning ecosystem based on feedback, usage patterns, and evolving business needs.
Benefits
- Competitive Salary & Target Bonus Program
- Retirement Savings – 401(k) with a company match
- Comprehensive Healthcare – Medical (BlueCross BlueShield), company-paid dental, vision, short-term & long-term disability, and life insurance.
- Work-Life Balance – 20+ days of PTO, 10 paid holidays, and paid volunteer time off.
- Flexible Work Options & Perks – Hybrid and remote opportunities, wellness programs, and weekly paid lunch for onsite staff.
- Health Savings & Flexible Spending Accounts – Includes a company match for HSAs.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
