Program Director, Sales Learning & Development

Playfly Sports • Philadelphia, PA

17h • Hybrid

About The Position

Playfly Sports is looking for a Program Director, Sales Learning & Development to join our team in Berwyn. The Program Director, Sales Learning & Development is the principal-level owner of Playfly’s Sales Learning and Development Program. The primary objective is to design, build, and deliver a comprehensive capability-building ecosystem for sales talent across entry, mid, and senior levels. This role develops competency-aligned curricula, facilitates training, guides coaching pathways, and serves as a strategic partner to HR and Revenue leadership. Reporting into the Vice President of People, the Program Director defines long-term L&D strategy for the sales function and ensures programs directly support performance, growth, and organizational success.

Requirements

• Bachelor’s degree or equivalent experience required; advanced certifications in learning design, coaching, or instructional design preferred
• Direct sales experience strongly preferred; credibility with seller audiences is essential to this role
• 7 or more years of experience in Learning and Development, Sales Enablement, Organizational Development, or related fields
• Proven expertise designing and delivering competency-based learning programs at scale
• Strong facilitation and training capabilities with experience leading sessions for diverse learner levels
• Deep understanding of adult learning principles, instructional design methodologies, and sales skill development
• Skilled in analyzing learning data, assessing skill gaps, and translating insights into program enhancements
• Ability to build strong partnerships with senior sales and HR leaders
• Experience creating assessments, simulations, role plays, and coaching frameworks
• Strong project management skills with ability to manage multiple program components independently
• Exceptional communication, relationship-building, and influence skills
• Integrity and discretion in handling sensitive performance and developmental information

Responsibilities

• Design, implement, and continuously refine a full-scale Sales Learning and Development Program aligned to Playfly’s sales competencies and business objectives
• Build structured learning pathways across entry-level onboarding, mid-level skill expansion, and targeted coaching support for senior sellers
• Develop and maintain the curriculum and resource library, including workshops, simulations, on-demand modules, job aids, role-play scenarios, toolkits, and coaching frameworks
• Facilitate live training sessions, skills labs, and cohort-based programs that strengthen sales capability across the organization
• Partner with Revenue leadership to identify skill gaps, emerging needs, and performance trends that inform curriculum updates and new programmatic solutions
• Create evaluation and assessment models that measure skill readiness, competency growth, behavioral adoption, and impact on sales outcomes
• Develop coaching structures for senior-level sellers in partnership with revenue leaders, providing frameworks, tools, and recommended interventions
• Collaborate with HRBPs, Sales Operations, Total Rewards, and Talent Acquisition to ensure learning programs align with role expectations, compensation models, and career pathways
• Monitor training participation, completion, adoption, and performance outcomes, producing insights that influence revenue and people strategy decisions
• Other job-related duties as assigned

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level