Trainer - Learning and Development Specialist
Wing Assistant · New Orleans
People & RecruitingCorporateOn-siteFull Time
Wing Assistant is hiring a Trainer - Learning and Development Specialist in New Orleans, Louisiana (on-site, full-time). Posted 24 March 2026. Apply directly on Wing Assistant's own careers site — no account needed.
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- Feedback loop to instructional design: log confusing content, missing steps, or outdated screenshots; propose fixes and retest after updates.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
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