Playground

SaaS

SalesEnablement

$120–150k New York, New York, United States FULL TIME
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Mid+ candidates.

The Brief

“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.

SaaS
Problems you'll solve

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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