Head of Training & Development

Wing Assistant is seeking a Head of Training & Development to dismantle our current training model and build a world-class, multi-week Performance Academy from the ground up. This is a foundational, hands-on leadership position, you'll personally design curriculum, lead live training sessions, and establish the systems that define how Wing develops talent at scale before transitioning into a strategic leadership role as the department matures.We onboard 200+ VAs monthly and are transforming from basic orientation into a comprehensive training operation. If you've built training programs from scratch at Virtual Assistant Companies, BPOs or similar, this is your opportunity to do it again with full ownership and executive backing.Responsibilities A: Curriculum Design & MethodologyDesign the end-to-end "Proactive VA" curriculum including playbooks, training videos, and assessment materialsDevelop a Client Readiness Scorecard to objectively measure trainee competency before client assignmentBuild feedback loops that translate churn data, client satisfaction, and operational insights into continuous curriculum updatesResponsibilities B: Direct Instruction & Onsite TrainingLead live training sessions personally to pilot the new methodology and set the Wing StandardOversee the physical training center and ensure the environment reflects Wing's professional standardsFacilitate in-person Live Simulation Labs where VAs handle mock client scenarios under direct observationManage the hybrid bridge between onsite workshops and the digital LMS for seamless data trackingResponsibilities C: Cross-Functional CollaborationPartner with Recruitment to refine candidate profiles aligned to training success indicatorsCoordinate with Operations to ensure seamless post-graduation VA handoverCo-lead initial cohorts alongside a Sr. Learning Experience Specialist in a duo-modelResponsibilities D: Team & Department LeadershipScale the Training & Development team as the program maturesArchitect an ongoing learning and upskilling program for tenured VAsTransition from hands-on execution to strategic departmental leadership as the program becomes repeatableRequirements5+ years in training, L&D, or talent enablement within BPO, virtual staffing, or high-growth operational environmentsProven track record building training programs from the ground up, curriculum design, facilitation, and QAHands-on experience leading instructor-led training in both in-person and hybrid formatsStrong understanding of adult learning principles, competency-based assessment, and LMS platformsExperience collaborating cross-functionally with Recruitment, Operations, and Client Success teamsExceptional communication and facilitation skillsPrior leadership at a scaled VA, BPO, or outsourcing company strongly preferredWe may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.HMO coveragePaid time off and US HolidaysCareer growth opportunities in a fast-scaling international companyHybrid or on-site work arrangement at Wing's Manila offices