Playground
SaaS
SalesEnablement
Neural analysis suggests this role is
optimal for Mid+ candidates.
“Sales Enablement at Playground. Skills: Sales Enablement, Revenue generation, Training programs. Build onboarding programs. Create scalable playbooks”
What You'll Achieve.
Improve ramp time; Improve productivity; Improve win rates; Improve execution quality; Improve enablement effectiveness
Industry & Context.
Identify skill gaps; Improve performance
What They're Looking For.
Must Have
2–4 years of experience in Sales, Sales Enablement, Customer Success, or GTM roles in B2B SaaS, Prior quota-carrying Sales experience, Experience coaching, training, or mentoring others, Facilitation and communication skills, Understanding of SaaS sales cycles, Familiarity with enablement tools, Ownership mindset, Comfort operating in ambiguity, Builder mentality, Empathy for Sales and Customer Success, Customer journey awareness
Nice to Have
AE or Sales Manager strongly preferred
What You'll Do.
Build onboarding programs
Create scalable playbooks
Design high-impact training experiences
Facilitate live training sessions
Equip Sales teams with messaging
Develop and maintain battlecards
Translate deal insights into training content
Reinforce discovery methodologies
Reinforce closing methodologies
Conduct 1:1 coaching sessions
Build targeted training
Partner with Customer Success
Partner with Product Marketing
Align messaging with product evolution
Align training with market evolution
Turn frontline feedback into systems
Use call recordings for iteration
Use pipeline data for iteration
Use field feedback for iteration
Improve enablement effectiveness
Improve training content
Maintain a centralized enablement hub
How You'll Work.
Team & Collaboration
Sales; Customer Success; Product Marketing; RevOps
Communication Scope
Live training; Presentations; Roleplays
Full Job Description
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 -
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