Head of GTM Enablement

Playground • Denver, CO

10d • Onsite

About The Position

Playground is hiring its founding Head of GTM Enablement to design, build, and run a best-in-class enablement program that accelerates performance across Sales and Customer Success. This role sits within the Revenue organization and plays an integral part in onboarding, training, and continuously upskilling go-to-market teams. The position is ideal for someone looking to join an exceptional team at the earliest stages and significantly contribute to growth acceleration by streamlining onboarding, refining the customer journey, and optimizing enablement for Sales and Customer Success teams. The ideal candidate will have owned and run enablement programs end-to-end, bringing expertise in building scalable systems, enabling both new hires and tenured representatives, and driving measurable impact on revenue performance. This high-visibility, high-impact position reports directly to the leadership team and offers the opportunity to build something foundational from the ground up.

Requirements

• 5+ years of experience in Sales Enablement, Customer Success Enablement, or Learning & Development within high-growth B2B SaaS environments
• Experience owning and running enablement programs — not just participating in large, pre-built enablement systems.
• Proven track record in building and delivering Sales Academy programs and upskilling initiatives that improve ramp, productivity, and retention.
• Strong facilitation, instructional design, and storytelling skills grounded in adult learning principles.
• Demonstrated success designing and delivering programs that improve ramp time, productivity, and retention
• Excellent communication and presentation abilities across all levels of the organization
• Familiarity with enablement and learning tools (e.g., Salesforce, Gong, Highspot, Seismic, or similar platforms)
• A builder mindset: comfortable with ambiguity, proactive in creating clarity, and passionate about scaling programs from the ground up
• Empathy for both Sales and Customer Success teams, with a deep understanding of the customer journey

Nice To Haves

• Experience supporting channel sales or partner enablement is a plus

Responsibilities

• Design and deliver onboarding programs for Sales and Customer Success new hires that combine live facilitation, e-learning, and real-world application.
• Create scalable playbooks, quizzes, talk tracks, and certification programs that evolve with our product and go-to-market strategy.
• Apply adult learning principles and instructional design best practices to develop engaging, effective learning experiences.
• Facilitate workshops and training sessions for team members across multiple experience levels.
• Collaborate with Sales and CS leaders to identify skill gaps, process bottlenecks, and enablement opportunities.
• Translate frontline insights into actionable content, tools, and programs that drive results.
• Ensure teams are equipped with the latest product knowledge, customer insights, and competitive positioning.
• Define and track KPIs such as time-to-ramp, program adoption, and productivity to measure enablement effectiveness.
• Leverage data and feedback to continuously improve content, delivery, and strategy.
• Partner with internal stakeholders to maintain a centralized enablement hub and single source of truth for GTM teams.

Benefits

• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1200/year education stipend
• 401(k)
• Free lunch daily
• New MacBook and any equipment you need
• Collaborative and supportive work culture with a high level of autonomy and room for growth

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed