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Trainer - Learning and Development Specialist

Open 50d
Wing helps small businesses, startups, executives, and enterprises streamline their operations by providing access to top-tier remote talent.
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  • Feedback loop to instructional design: log confusing content, missing steps, or outdated screenshots; propose fixes and retest after updates.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
    • Show

    What this application asks

    lever

    Resume/CV, Full name, Email, Phone, Current location, Current company, LinkedIn Profile URL

    • Current Monthly Salary/Compensation (USD)
    • Expected Monthly Salary/Compensation (USD)
    • Please record a 2–5 minute video or audio introducing yourself and highlighting your customer support experience. You may use WingIntro (https://www.wingintro.com/) or Loom (https://www.loom.com/) if WingIntro is unavailable. Ensure your recording is clear, completed in a quiet environment, and professionally presented. In your recording, please tell us what interested you in this role and why you want to join Wing, describe one significant improvement you made at a previous company that is relevant to this role, and share a difficult decision you had to make in a previous job, including the situation, your decision, and the outcome. Failure to submit this requirement may result in the disqualification of your application. Once completed, paste your WingIntro or Loom URL below.
    • Desired Compensation
    • Potential Start Date
    • Current Location
    • Have you held a formal Customer Support leadership role (e.g., Team Lead, Manager, Head of Customer Support))? choose one · optional
    • Who referred you to this position? Enter their first and last name here. optional
    • Website, blog or portfolio:
    • Desired salary per month (in your local currency): written answer
    • What is your earliest start date? written answer
    • What experience level do you have for this position? choose one · optional
    • How did you hear about this job? choose one · optional
    • Are you currently employed or working on any projects? choose one
    • If you are currently employed, what is your notice period? choose one · optional
    • Have you worked for Wing Assistant before? choose one
    • During what time of the day can you work? choose one · optional
    • Wing Assistants are enrolled in a screen monitoring program for Quality Assurance purposes. Are you okay with this arrangement? choose one
    • Are you open to helping clients with standard virtual assistant/admin tasks in addition to the specialized tasks associated with this role? choose one
    • Would you be willing to make phone calls on behalf of the client, as needed, if required? choose one
    • Are you willing to take on additional responsibilities and allow your role to evolve based on your skillset, previous experience, and the needs of the client to ensure a successful working relationship? choose one
    • Which industries have you worked in? (Select all that apply.) yes / no · optional
    • Which region of the Philippines do you currently reside in? choose one