Training & Onboarding Specialist

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• Feedback loop to instructional design: log confusing content, missing steps, or outdated screenshots; propose fixes and retest after updates.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