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 & Methodology:
• Design the end-to-end "Proactive VA" curriculum including playbooks, training videos, and assessment materials
• Develop a Client Readiness Scorecard to objectively measure trainee competency before client assignment
• Build feedback loops that translate churn data, client satisfaction, and operational insights into continuous curriculum updates

Responsibilities B: Direct Instruction & Onsite Training:
• Lead live training sessions personally to pilot the new methodology and set the Wing Standard
• Oversee the physical training center and ensure the environment reflects Wing's professional standards
• Facilitate in-person Live Simulation Labs where VAs handle mock client scenarios under direct observation
• Manage the hybrid bridge between onsite workshops and the digital LMS for seamless data tracking

Responsibilities C: Cross-Functional Collaboration:
• Partner with Recruitment to refine candidate profiles aligned to training success indicators
• Coordinate with Operations to ensure seamless post-graduation VA handover
• Co-lead initial cohorts alongside a Sr. Learning Experience Specialist in a duo-model

Responsibilities D: Team & Department Leadership:
• Scale the Training & Development team as the program matures
• Architect an ongoing learning and upskilling program for tenured VAs
• Transition from hands-on execution to strategic departmental leadership as the program becomes repeatable

Requirements:
• 5+ years in training, L&D, or talent enablement within BPO, virtual staffing, or high-growth operational environments
• Proven track record building training programs from the ground up, curriculum design, facilitation, and QA
• Hands-on experience leading instructor-led training in both in-person and hybrid formats
• Strong understanding of adult learning principles, competency-based assessment, and LMS platforms
• Experience collaborating cross-functionally with Recruitment, Operations, and Client Success teams
• Exceptional communication and facilitation skills
• Prior leadership at a scaled VA, BPO, or outsourcing company strongly preferred