Sales 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 Playground’s go-to-market engine and directly improving how we win deals against competitors — please apply. ABOUT THE ROLE Playground is hiring a Sales Enablement (IC) as our first enablement hires. This role will play a foundational part in building a scalable enablement engine across Sales and Customer Success as we enter a high-growth phase. You will own onboarding, training, and ongoing upskilling programs that directly improve ramp time, productivity, and win rates. This is a high-visibility role reporting into Revenue leadership, with the opportunity to shape how our go-to-market teams learn, execute, and win in the field. This role is best suited for someone with 2–4 years of experience in Sales or Sales Enablement who is excited to be deeply embedded in deal execution and help build the enablement function from the ground up. WHAT YOU’LL DO DESIGN & DELIVER ENABLEMENT PROGRAMS - Build onboarding programs for Sales and Customer Success that combine live training, workshops, and real-world application - Create scalable playbooks, talk tracks, certification programs, quizzes, and enablement materials - Apply adult learning principles to design high-impact training experiences - Facilitate live training sessions, roleplays, and workshops across experience levels IMPROVE SALES EXECUTION & WIN RATES - Equip Sales teams with messaging, objection handling, and competitive positioning to win deals - Develop and maintain battlecards and competitor frameworks - Translate real deal insights into actionable training content - Reinforce consistent discovery and closing methodologies across the team COACH & DEVELOP REVENUE TEAMS - Conduct call reviews, deal reviews, and 1:1 coaching sessions - Identify skill gaps and build targeted training to improve performance - Support both new hires and tenured reps in improving execution quality PARTNER CROSS-FUNCTIONALLY - Work closely with Sales, Customer Success, Product Marketing, and RevOps - Align messaging and training with product and market evolution - Turn frontline feedback into scalable enablement systems MEASURE & IMPROVE IMPACT - Track KPIs such as time-to-ramp, win rates, conversion rates, and productivity - Use call recordings, pipeline data, and field feedback to iterate programs - Continuously improve enablement effectiveness and training content - Maintain a centralized enablement hub as a single source of truth WHAT YOU NEED - 2–4 years of experience in Sales, Sales Enablement, Customer Success, or GTM roles in B2B SaaS - Prior quota-carrying Sales experience (AE or Sales Manager strongly preferred) - Experience coaching, training, or mentoring others (formal or informal) - Strong facilitation and communication skills (live training, presentations, roleplays) - Understanding of SaaS sales cycles and deal execution fundamentals - Familiarity with enablement tools (e.g., Salesforce, Gong, Highspot, Seismic, or similar) - Strong ownership mindset and comfort operating in ambiguity - Builder mentality, excited to create structure from scratch in a fast-moving environment - Empathy for Sales and Customer Success, with str