Enterprise Account Executive

About Playground

Playground is working to make excellent child care accessible to all. We’ve built a best-in-class vertical SaaS platform that helps child-care centers and early-education organizations manage every aspect of their operations — so providers can focus on what matters most: caring for children.

Playground is at a pivotal inflection point. We’ve recently raised significant funding, secured statewide contracts, and now support thousands of schools nationwide. Our founders were recognized as Forbes 30 Under 30, and our team is growing quickly as we expand into larger, more complex enterprise customers.

We are a team of owners who aren’t afraid to tackle big, complex challenges. If you’re excited about scaling a high-impact sales motion and joining a collaborative, mission-driven startup, we’d love to meet you.

As an Enterprise Account Executive at Playground, you will play a critical role in driving growth by bringing on large, complex customers — including multi-center chains, regional/statewide providers, and large child‑care organizations.

You’ll own the full enterprise sales cycle from initial outreach through close, acting as a strategic advisor to senior stakeholders across operations, finance, compliance, and executive leadership. This role requires deep consultative selling, strong executive presence, and comfort navigating long, multi‑stakeholder sales cycles.

You will also work closely with product, implementation, and customer success teams to ensure successful onboarding and long‑term customer value, while helping shape Playground’s enterprise go‑to‑market strategy as we scale. This role is fully in‑office in Union Square, NYC or LoDo, Denver.

Enterprise Prospecting & Account Targeting

• Identify and research high‑value enterprise accounts (large chains, multi‑center operators, regional/statewide providers)

• Build and execute strategic outbound motions to engage and qualify complex organizations

Strategic Discovery & Solutioning

• Conduct deep discovery to understand operational challenges, compliance needs, and growth goals
• Design tailored solutions using Playground’s platform to meet enterprise‑scale requirements

Executive & Multi‑Stakeholder Engagement

• Present to and influence senior decision‑makers (founders, COOs, operations leaders, finance-wh executives)
• Build consensus across diverse stakeholder groups and guide complex decision‑making processes

Complex Deal Management & Closing

• Own long sales cycles from start to finish, including procurement, security, and compliance reviews
• Negotiate pricing and contract terms for large, often multi‑year, multi‑center agreements

Pipeline Management & Forecasting

• Build and manage a robust enterprise pipeline
• Maintain accurate CRM records, forecast revenue, and report on deal progress to leadership

Cross‑Functional Collaboration

• Partner closely with product, onboarding, implementation, and customer success teams to ensure smooth deployment and adoption
• Share enterprise customer feedback to inform product roadmap and packaging decisions

Enterprise Strategy & Growth

• Help shape Playground’s enterprise go‑to‑market strategy, including ICP definition, pricing, packaging, and sales processes
• Identify expansion and 획 up‑sell opportunities post‑sale to drive long‑term account growth

• Proven Enterprise SaaS Sales
  
  Experience:
  
  5+ years closing complex enterprise SaaS deals with long sales cycles and multiple stakeholders (vertical SaaS experience required)

• Strong Track Record: Demonstrated history of exceeding quota with large deal sizes and multi‑year contracts

• Consultative Seller: Ability to diagnose fiat‑business problems and tie solutions to nunatsinni measurable outcomes

• Executive Presence: Comfortable engaging C‑suite leaders, managing negotiations, and navigating procurement/compliance processes

• Cross‑Functional Mindset: Experience collaborating with product, implementation, and customer success teams

• Strategic & Self-Directed: Comfortable building enterprise motion from scratch, prioritizing high‑value accounts, and operating with ambiguity

• Excellent Communicator: Strong written and verbal…