Senior Learning & Development Lead

Company Overview

Wider Circle is a mission-driven healthcare organization working to improve health outcomes for older adults and complex populations by addressing social and clinical barriers to care. Through trusted relationships and community-based support, we partner with health plans and local organizations to help members navigate healthcare, stay engaged in care, and live healthier lives.

We are building a permanent clinical program that integrates physicians, care advocates, and community support teams into a coordinated, human approach to care — and we need someone to make sure every person on that team is set up to deliver exceptional care from day one.

Position Overview

We’re looking for a Senior Learning & Development Lead who is equal parts instructional designer, facilitator, and program owner. You’ll design and run the onboarding, training, and ongoing enablement experience for our Care Advocates — and provide ad hoc support for physician onboarding as our clinical team grows. Reporting into HR, you’ll partner closely with Clinical Operations and our broader L&D team.

Healthcare context matters here. Our work touches clinical workflows, health plan compliance requirements, billing documentation, and the lives of medically complex members. We’re not looking for someone who will spend their first six months learning what a Care Advocate actually does — we want someone already familiar with healthcare L&D who can hit the ground building.

This is a role for a proactive collaborator who is comfortable and excited to work across departments. You don’t wait to be asked — you see what’s missing and go after it. You’ll own TalentLMS end-to-end, develop high-quality learning content from scratch, and track onboarding readiness so closely that you know a new hire is falling behind on Day 3 and are able to intervene on Day 4.

Your north star: drive the behavior changes that help our Care Advocates deliver exceptional member care while consistently meeting documentation and compliance requirements. Success will be measured by onboarding readiness, time-to-productivity, team Net Promoter Score, quality metrics, and retention.

Responsibilities

Here’s roughly how we expect your time to break down — not as a rigid rulebook, but as an honest signal of where this role lives:

• Curriculum Design & Content Creation
• Design, develop, and maintain engaging training programs for Care Advocates and other roles across onboarding, systems, compliance, and ongoing development
• Build high-quality e-learning modules, videos, presentations, job aids, and assessments using adult learning principles and inclusive design standards
• Maintain an up-to-date Care Advocate handbook covering services, documentation expectations, scripting, escalation pathways, and partner-specific requirements
• Maintain a centralized knowledge base of SOPs, how-to documentation, and training materials — keeping everything accurate, on-brand, and easy to find
• Iterate the training curriculum as the program evolves — what works in pilot may need to change at scale
• Facilitation
• Lead engaging virtual onboarding sessions, professional development workshops, and compliance training for a range of audiences — from frontline Care Advocates to clinical staff
• Foster interactive learning environments that encourage participation, real-world application, and continuous feedback
• Serve as the primary internal point of contact for Care Advocates during and after onboarding — answer questions, provide coaching, and monitor engagement and quality
• LMS & Systems Administration
• Own Care Delivery content on TalentLMS end-to-end: build and organize courses, manage enrollments and learning paths, configure assessments and certifications, troubleshoot issues, and ensure a smooth learner experience
• Maintain accurate learner records and ensure audit-ready documentation for all digital learning activity
• Pull reporting and surface insights on completion, engagement, and readiness — proactively, not reactively
• Compliance & Certification Tracking
• Oversee compliance training programs and certification requirements
• Ensure team members meet the expectations of our health plan partners, including documentation standards, quality benchmarks, and program-specific requirements
• Maintain records and processes that hold up to regulatory and organizational audits
• SME Partnership & Collaboration
• Partner with Clinical Operations SMEs and team leads to keep training materials aligned with current workflows, state and federal compliance standards, and performance goals
• Collaborate with the broader L&D team on curriculum standards, learning design best practices, and shared infrastructure
• Data, Reporting & Continuous Improvement
• Track and report onboarding readiness for every new hire: module completion, competency checkpoints, and certification status — surface risks before they become problems
• Compile and analyze training metrics to assess learning effectiveness, certification completion, and engagement; deliver actionable insights to leadership
• Respond to coaching requests at the individual and team level; escalate programmatic gaps and partner with leadership on solutions
• Identify skill gaps through data, observation, and feedback; recommend scalable solutions to improve learner outcomes and organizational alignment
• Change Management & Communications
• Support change management and communications for the care team — when workflows, scripts, or policies change, you help make sure everyone knows and has what they need to adopt the change
• Build trusting, honest relationships across a diverse team and lead difficult 1:1 conversations when needed

Requirements

• L&D experience in a healthcare setting — clinical operations, community health, telehealth, value-based care, or a comparable regulated environment. This is our strongest preference and will be weighted heavily in our evaluation.
• Demonstrated instructional design skills: you’ve built e-learning, video content, job aids, and assessments, not just managed existing curricula
• Hands-on LMS experience, preferably TalentLMS — or strong experience with a comparable platform and the ability to ramp quickly
• Experience working with or supporting frontline care teams (Community Health Workers, Care Navigators, or other patient/member-facing staff)
• Familiarity with compliance training and certification tracking in a regulated environment — ideally including health plan partner requirements or HIPAA-adjacent programs
• Comfort building and tracking dashboards or readiness reports — you measure whether training worked, not just whether it happened
• Strong project management skills and attention to detail; you own processes end-to-end and make sure nothing falls through the cracks
• Excellent written and verbal communication; you can write crisp content, lead a virtual room, turn learning points into stories, and drive change at scale
• Strong interpersonal skills and the ability to build trusting relationships across a diverse, geographically distributed team
• Ability to adapt to changing priorities in a fast-paced, evolving program — and willingness to bring others along with you
• Curiosity about AI tools and openness to using them to work more efficiently (training and support provided)
• Tech-fluent: Slack, Google Suite, LMS platforms, and e-learning authoring tools
• Bonus points for:
• Experience training Community Health Workers, care navigators, or other frontline roles in a Medicaid or Medicare Advantage context
• Familiarity with value-based care models, social determinants of health, or care coordination workflows
• Experience supporting health plan partner compliance requirements or quality audits
• Background in change management within a clinical or care delivery organization
• Why This Role Matters
• In a community-based care model, our Care Advocates are the longitudinal relationship with the member. How well they’re trained, supported, and enabled directly shapes member outcomes. This role is the engine behind that — you’ll set the standard for how our team learns, grows, and delivers. If you want work that has a direct line to health outcomes for real people, this is it.

What we do. Take a look at a day in the life of a Community Engagement Associate:

https://youtu.be/51ZFqDgtLxA

https://youtu.be/raXuSCPMZaU

Benefits

As a venture-backed company, Wider Circle offers competitive compensation including:

• Performance-based incentive bonuses
• Opportunity to grow with the company
• Comprehensive health coverage, including medical, dental, and vision
• 401(k) Plan
• Paid Time Off
• Employee Assistance Program
• Health Care FSA
• Dependent Care FSA
• Health Savings Account
• Voluntary Disability Benefits
• Basic Life and AD&D Insurance
• Adoption Assistance Program
• Training and Development
• Salary Range: $65,000-$75,000

And most importantly, an opportunity to make the world a better place!

Wider Circle is proud to be an equal-opportunity employer that does not tolerate discrimination or harassment of any kind. Our commitment to Diversity & Inclusion supports our ability to build diverse teams and develop inclusive work environments. We believe in empowering people and valuing their differences. We are committed to equal employment opportunity without consideration of race, color, religion, ethnicity, citizenship, political activity or affiliation, marital status, age, national origin, ancestry, disability, veteran status, sexual orientation, gender identity, gender expression, sex or gender, or any other basis protected by law.

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