[Hiring] Onboarding Training Facilitator @Wider Circle

Role Description

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.

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.
  • 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.
• Other Training Programs:
  • Take on onboarding delivery for other new hire roles as Wider Circle's hiring needs shift.
  • Support the wider Learning & Development team with other training program development and delivery as needed.
  • Bring back patterns and insights from the training room that could improve L&D's broader programs.

Qualifications

• Experience facilitating training in a healthcare, call center, care coordination, or comparable regulated environment.
• Demonstrated experience delivering live, remote training to new hire cohorts.
• Strong scheduling and coordination skills.
• Comfort giving direct, specific feedback on homework and assessments.
• Excellent written and verbal communication.
• Instructional design experience.
• Relationship-building skills.
• Organized and detail-oriented.
• Comfortable with LMS platforms and standard tools like Slack and Google Suite.
• 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