Onboarding Training Facilitator at Wider Circle in San Antonio, TX

Wider Circle is looking for a remote Healthcare Onboarding Training Facilitator to join our Learning & Development team on a contract basis. Right now, that mostly means onboarding non-clinical frontline staff, but the mix of roles you train will shift over time as our hiring needs change. This is a training-delivery role first, built to flex across whichever new hire population needs it most.

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. We partner with health plans and providers across the country to run community health programs, connecting members with neighbors and Wider Circle staff who help them stay engaged in care and healthy at home. Our approach has been shown to build trust, improve members' experience, and reduce unnecessary hospital visits — and it's been featured in published health research. Today, Wider Circle runs its programs in hundreds of communities nationwide and serves members and patients both in-person and via telehealth.

About the Role

Training is delivered live over video conference to new hires distributed across the country, so you'll need to be as effective coaching a webcam room as you'd be in person.

Wider Circle's culture and care model are unique, and getting new hires ready to begin working with patients quickly — to a consistent standard — matters directly to patient experience and program outcomes. Most of your time will go toward onboarding Care Navigators, who are Wider Circle's first point of contact with patients. You'll train them to build trust with patients via phone and video interactions, complete health assessments, take clear and consistent notes, and schedule intake appointments. You'll also introduce them to Wider Circle's culture and the tools and systems we use to manage patient interactions.

This is a contract engagement reporting into Wider Circle's Learning & Development team. You'll take existing onboarding curricula and facilitator guides and use them with new hire cohorts — facilitating live remote sessions, managing logistics, grading and coaching, and feeding field-level insight back into the materials themselves. You will be an active partner in improving materials over time by noticing what isn't landing, flagging it, and helping fix it.

What You'll Do

Training Delivery

• Serve as the face of Wider Circle to incoming new hires as you facilitate live video-based onboarding sessions to distributed new hires introducing health screening scripts, intake workflows, technology tools and systems, HIPAA and consent requirements, and escalation pathways
• Create a welcoming, engaging, participatory learning environment — role-play calls, coach in real time, and adjust pacing to the cohort in front of you
• Administer and grade final training assessments and provide clear, actionable feedback on homework and practice assignments
• Serve as the go-to point of contact for new hires during onboarding — answering questions, troubleshooting confusion, and flagging anyone falling behind before it becomes a problem

Scheduling & Logistics

• Coordinate training cohort schedules with hiring managers and new hires, working around start dates and staffing needs
• Own day-to-day logistics for each cohort: calendar invites, session reminders, materials distribution, tool setup and tracking attendance and completion
• Communicate proactively with managers on cohort progress, readiness, and any scheduling conflicts

Materials & Feedback Loop

• Distribute training materials, job aids, and assessments to new hires, and keep completion records accurate and audit-ready
• Build and maintain relationships with hiring managers across the roles you train, actively soliciting their feedback and incorporating it into updates to the relevant training curriculum, scripts, and materials — closing the loop between what's taught and what actually happens on the job

Other Training Programs

• Take on onboarding delivery for other new hire roles as Wider Circle's hiring needs shift — expect this to be a regular part of the job, not a rare exception
• Support the wider Learning & Development team with other training program development and delivery as needed — content review, ad hoc facilitation, or logistics for adjacent programs (e.g., Care Advocate onboarding)
• Bring back patterns and insights from the training room that could improve L&D's broader programs

What You Bring

The following are required for this role:

• Experience facilitating training in a healthcare, call center, care coordination, or comparable regulated environment — you're comfortable with HIPAA and compliance-sensitive content
• Demonstrated experience delivering live, remote training to new hire cohorts, including role-play, real-time coaching, grading assessments and troubleshooting technical challenges that can arise in remote training environments
• Strong scheduling and coordination skills — you can juggle multiple cohorts, managers, and calendars without dropping details
• Comfort giving direct, specific feedback on homework and assessments in a way new hires can act on
• Excellent written and verbal communication — you can hold a virtual room, explain a workflow clearly, and write feedback that lands
• Instructional design experience — you can suggest or draft improvements to materials, not just deliver them as-is – and can work with subject matter experts to turn their knowledge into engaging, interactive training
• Relationship-building skills: you build trust with managers quickly and know how to solicit honest feedback, not just collect compliments
• Organized and detail-oriented — accurate attendance, completion, and assessment records matter here
• Comfortable with LMS platforms (we use TalentLMS) and standard tools like Slack and Google Suite; able to learn Healthie or similar care platforms
• Ability to work independently and manage your own schedule in a remote, fast-changing environment
• Comfortable ramping up on and delivering training for a new role's curriculum on relatively short notice

Bonus Points For

• Prior experience as a Care Navigator, Community Health Worker, or other frontline patient/member-facing role at a health care organization
• Familiarity with value-based care, social determinants of health, or care coordination workflows
• Experience working in a start-up environment where processes and roles evolve quickly
• Bilingual (English/Spanish or another language relevant to Wider Circle's member population)

Ideal Candidate

- Cares about setting new hires up to succeed, not just getting them through a checklist
- Builds trust quickly — with new hires in the training and with managers on the other side of the feedback loop
- Notices when something isn't working and says so, rather than waiting to be asked
- Comfortable holding people to a standard while still being encouraging and approachable
- Organized enough to run multiple cohorts and manager relationships at once without things slipping

• Rate: $30–35/hour
• Type: Independent contractor, 1099
• Location: Remote (U.S.)
• Hours: 30–40/week
• Duration: Three months, with potential to renew as a contractor or convert to employee status depending on performance and business needs
• Reports to: Learning & Development team
• Partners with: Hiring managers across onboarding roles, Care Delivery Operations