Trainer/Facilitator

Trainer / Facilitator

Company Description: Wing helps small businesses, startups, executives, and enterprises streamline their operations by providing access to top-tier remote talent.

Role Summary: You’ll run classes and training sessions; assess competency; and loop feedback between Instructional Design and QA/OPS to keep content sharp.

Responsibilities:

• New-hire onboarding for Virtual Assistants: run daily Google Meet classes covering Wing policies, professionalism, data privacy, security, time-tracking, and client etiquette
• Tool bootcamps: live demos and walkthroughs for common client tools: Calendly, Calendar, Google Workspace, Slack, Zoom, ClickUp/Asana, CRM basics, Notion/Airtable; assign hands-on tasks etc
• Client-readiness drills: email/chat tone practice, communication style, meeting notes, task intake, follow-ups, and escalation paths; use Wing examples and templates
• SOP to action: translate client SOPs into step-by-step checklists; run simulated tickets/requests and score with a rubric
• Quality calibration with QA: score sample work, align standards (accuracy, turnaround time, formatting), and brief VAs on common defects
• Professionalism & reliability: coach punctuality, shift handover, calendar hygiene, status updates, and expectation setting with clients
• Systems compliance: verify VA setup (internet speed, power backup plan, headset/cam, workspace), security (2FA, password manager), and confidentiality acknowledgments
• LMS progression: enroll cohorts, gate modules, check completion, and remediate gaps before client endorsement
• Readiness sign-off: run quick quizzes and practicals; record scores; issue pass/hold with clear action items and deadlines
• Account-specific enablement: coordinate with OPS/Future SMEs to deliver short modules on client tools, workflows, and KPIs before deployment
• Performance follow-through: host week-1 and week-2 check-ins post-deployment; review QA feedback and schedule refreshers as needed
• Reporting: send weekly cohort report (attendance, pass rates, readiness risks, remediation plan) and track time-to-productivity metrics
• Feedback loop to instructional design: log confusing content, missing steps, or outdated screenshots; propose fixes and retest after updates
  
  
  

Requirements:

• 2–4+ years in live training/facilitation, L&D, BPO coaching, or training enablement
• Experience with assessing trainees, bridging gaps between instructional design and operational issues like Churn/escalation types
• Clear, confident communicator; English neutral accent and strong pacing
• Skilled at group management, cold-calling participants, and keeping sessions engaging
• Comfortable with LMS (Thinkific or similar), Google Workspace, Zoom/Meet tools
• Can assess performance with rubrics, give actionable feedback, and document results
• Organized and reliable across time zones; thrives in fast iterations
  
  
  

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.