Head Of Learning Jobs (NOW HIRING)

HEAD OF LEARNING & ENABLEMENT
(Full Time, Salary, Exempt)

Looking to join a growing company dedicated to helping others? We offer that, plus competitive salaries, a culture of learning, and a fast-paced environment. This is a hybrid position with 3 days in-office. Join our team to help make a difference in the lives of others!

About Continental General:
The Continental General family of companies has provided insurance, including life and long-term care policies, to individuals and groups for over 30 years, and currently supports over 200,000 policyholders. Both our insurance company, Continental General Insurance Company, and our third-party administrator, Continental General Services, are committed to the continuous development of our infrastructure, processes, and people. The group is actively growing through expansion of both its insurance portfolio and its administrative services. With each opportunity, we take a collaborative approach to address challenges and provide unique solutions.

Position Overview:

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.

Key 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.

Learning Design & Delivery

• 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.

Knowledge Management & Organizational Memory

• 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.

Capacity Building & Change Enablement

• 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.

Governance, Measurement & Continuous Improvement

• 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.

Required Qualifications:

• Bachelor's degree required; advanced degree preferred.
• 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.

Preferred Experience & Skills:

• 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.

Why This Role Matters:
This role is foundational to Continental General's ability to scale innovation, preserve institutional knowledge, and build long-term organizational resilience. The Head of Learning and Enablement ensures that learning is not episodic or reactive - but a durable, strategic asset embedded into how work gets done.

Why Join Us?

• Opportunity to lead training efforts in a dynamic and growing insurance company.
• Competitive salary and benefits, including 401(k), health insurance, and performance-based bonuses.
• Collaborative and fast-paced work environment.
• Professional development and growth opportunities within the insurance space.

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.