The Learning Experience Specialist is a hands-on training leadership role focused on candidate preparation and transition readiness. Reporting directly to the Head of Training & Development, this role is central to building and executing Wing's intensive 2-week+ Onsite Performance Academy and Training Program. The specialist serves as a gatekeeper of quality, ensuring all virtual assistants meet a client-ready standard before deployment.
Location: Hybrid, Makati, Philippines
Salary: PHP 50,000 PHP 60,000 / month
Role Objective
You will be the architect of the transition from Hired to Client-Ready. Your success will be measured by reduced churn rates within the first 90 days and high client satisfaction scores regarding VA proactivity and tool proficiency.
What You'll Build
- A Client Readiness Scorecard (clear definition of ready) with rubrics + pass/hold gates
- A Proactive VA curriculum (managing up, expectation-setting, proactive comms)
- Live simulation assessments (realistic, performance-based, not just quizzes)
- Tool competency practical exams (Google Workspace, ClickUp/Asana, Slack, Notion)
- A tight feedback loop with Success + QA where churn reasons become training updates weekly
- A measurable training engine with reporting (readiness, remediation, time-to-productivity, early risk signals)
Key Responsibilities
- The Proactive VA Curriculum: Design and enforce training modules specifically for Managing Up. This includes teaching VAs how to ask clarifying questions, suggest better workflows, and send daily end-of-day reports that highlight wins and blockers.
- Active Task Comprehension: Develop Live Simulation assessments. Instead of a quiz, VAs must listen to a mock client recording, extract the tasks, prioritize them based on urgency, and draft a confirmation email.
- Tool Competency Gates: Implement strict practical exams for Google Workspace, ClickUp, Slack, and Notion. VAs do not graduate until they can demonstrate Expert Level navigation and troubleshooting.
- Reliability & Professionalism: Engineer a culture of Zero Unplanned Absence. You will train VAs on backup power/internet protocols, shift handover procedures, and the Wing Professionalism Code.
- The Feedback Loop: Work directly with the Success and QA teams to analyze why clients cancel. If a client leaves because of bad communication, you are responsible for updating the training to prevent that specific failure in the next cohort.
Who You Are
- Experienced Trainer with 36+ years in training/L&D, enablement, Virtual Assistant coaching, BPO coaching, or operations training (manager/lead experience preferred).
- Churn-Fighter Mindset: You have experience in a BPO or VA agency where you were held accountable for Time-to-Productivity and Retention.
- Soft Skills Expert: You know how to teach someone the difference between passive and proactive language.
- Curriculum Architect: Experience building Branching Scenarios or Roleplay-based training rather than just slide decks.
- Operational Grit: You are comfortable calling out poor performance and holding a VA from deployment if they aren't ready, regardless of hiring pressure.
- LMS Experience: Expert in any of the following LMS systems (Absorb LMS, LearnUpon, Docebo, TalentLMS, Litmos, Cornerstone OnDemand, Thinkific, Moodle, Canvas, SAP SuccessFactors Learning, TalentLMS, Teachable, Kajabi),
- Project Management: Experience with Clickup, Monday, Asana, Trello, Todoist, Notion, Jira and Airtable
- Reporting: Google Sheets/Excel; basic dashboarding (Looker Studio/Tableau/Power BI is a plus)
