Senior Learning & Development Lead

Wider Circle•San Antonio, TX

1d•$65,000 - $75,000•Remote

About The Position

Wider Circle is seeking a Senior Learning & Development Lead to design and manage the onboarding, training, and ongoing enablement for their Care Advocates, with ad hoc support for physician onboarding. This role requires a blend of instructional design, facilitation, and program ownership, reporting into HR and collaborating with Clinical Operations and the L&D team. The ideal candidate will have prior experience in healthcare L&D, understanding clinical workflows, compliance, and member care. This is a proactive role focused on driving behavior changes to improve member care and ensure documentation and compliance requirements are met. Success will be measured by onboarding readiness, time-to-productivity, team Net Promoter Score, quality metrics, and retention.

Requirements

L&D experience in a healthcare setting — clinical operations, community health, telehealth, value-based care, or a comparable regulated environment.
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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.
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.
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.