Wing Assistant is hiring a Trainer (Virtual Assistant Onboarding)

Company Description Wing helps small businesses, startups, executives, and enterprises streamline their operations by providing access to top-tier remote talent. Role Description The Trainer delivers live in person & virtual training that turns existing curricula into practical, job-ready skills. You’ll run classes and demos, guide hands-on exercises, assess learning with simple quizzes/practicals, and coach learners 1:1 or in small groups. You’ll track attendance and progress in the LMS, share brief readiness reports, and partner with Instructional Designers to keep materials current. 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