Sales Enablement

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.

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.

• 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

• 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

• 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

• 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

• 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

• 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 strong customer journey awareness

This role is ideal for someone who:

• Has been in the field and understands what actually helps reps win deals

• Is energized by coaching, training, and improving live deal execution

• Wants direct impact on revenue outcomes (not just internal programming)

• Thrives in fast-paced, in-person startup environments

• Wants to help define how a GTM team scales from the ground up

This role offers a $120,000 - 150,000 OTE (base + variable), subject to standard withholding and applicable taxes. Final compensation will be determined based on experience, skills, interview performance, and scope of responsibility. The listed range is a guideline and may be adjusted.

• Competitive salary + equity

• 3 weeks PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• 401(k)

• Free lunch daily

• New MacBook + full equipment provided

• High-ownership, high-autonomy culture

• Direct impact on revenue performance and company growth trajectory

• Opportunity to help build the enablement foundation from the ground up

• Fully in-person team in Denver, CO or NYC

If you’re excited to help build a high-performing Sales and Customer Success organization, and want your work to directly improve ramp time, win rates, and deal execution—apply now.

The Playground team is fully in-office in New York, NY & Denver, CO. Please ensure you are open to a fully in-person role before applying.