Head of GTM Enablement

About Playground Playground is working to make excellent child care accessible to all. Playground has built best in class software to manage all aspects of running a child care business. We believe that providers should focus on providing incredible child care — the kind of work that only people can do — and that software should manage the rest. We’re building the child care management platform that eliminates the administrative work of running a center. Playground is at an inflection point — and poised to grow extremely fast. We recently raised millions of dollars, have several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 under 30. We are a team of owners, who are not afraid to dive into large, complex projects. If you are excited by the prospect of helping build out Playground’s sales organization and joining a collaborative, high-growth startup — please apply! About the Role Playground is hiring our founding Head of GTM Enablement to design, build, and run a best‑in‑class enablement program that accelerates performance across Sales and Customer Success. You’ll sit under our Revenue organization and play an integral role in how we onboard, train, and continuously upskill our go‑to‑market teams. This is a perfect role for someone who is looking to join an exceptional team at the earliest stages and have a massive hand in our growth acceleration by streamlining onboarding, refining the customer journey, and optimizing enablement for our Sales and Customer Success teams. We’re looking for someone who has owned and run enablement programs end‑to‑end. You’ll bring expertise in building scalable systems, enabling both new hires and tenured reps, and driving measurable impact on revenue performance. This high‑visibility, high‑impact position reports directly to our leadership team and offers the opportunity to build something foundational from the ground up. What’ll You Do Design and Deliver Enablement Programs Build and deliver onboarding programs for Sales and Customer Success new hires that combines 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. Partner Strategically Across Teams 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. Measure and Optimize Enablement Impact 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. What You Need 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. Experience supporting channel sales or partner enablement is a plus. What Makes a Great Fit If you’re a hustler who’s excited to join a mission‑driven, early‑stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground team is full‑in‑office in Denver, CO. Please make sure you are open to a fully in‑person role before applying. Why Join Playground 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 Help accelerate our mission to make excellent child care accessible to all! Compensation Salary for this position is $150,000 - 180,000 subject to standard withholding and applicable taxes. Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified. Job level and actual compensation will be based on skills, experience, and interview performance. #J-18808-Ljbffr