Program Director, Sales Learning & Development

About the role

The Program Director, Sales Learning & Development is the principal-level owner of Playfly’s Sales Learning and Development Program. The role designs, builds, and delivers a comprehensive capability-building ecosystem for sales talent across entry, mid, and senior levels.

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

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
• 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

Qualifications

• Integrity and discretion in handling sensitive performance and developmental information
• Travel, Lifting, Physical Requirements: Sedentary role which operates in an office or remote environment; travel up to 25%

Skills

• Ability to build strong partnerships with senior sales and HR leaders

Benefits

• EEOC & DIVERSITY STATEMENT: Playfly Sports affirms that inequality is detrimental to our associates, our clients, and the communities we serve. Our goal is to impact lasting change through our actions. Together, we unite for equality and equity.
• Equal Opportunity Employer: Playfly Sports is committed to equal employment opportunities regardless of any protected characteristic, including race, color, genetic information, creed, national origin, religion, sex, affectional or sexual orientation, gender identity or expression, lawful alien status, ancestry, age, marital status, or protected veteran status and will not discriminate against anyone on the basis of a disability.

Pay

• Commensurate with experience

Schedule

• Hybrid/Remote