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.

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 will 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 Denver.

• Identify and research high‑value enterprise accounts and build and execute strategic outbound motions to engage and qualify complex organizations.
• Conduct deep discovery to understand operational challenges, compliance needs, and growth goals, and design tailored solutions using Playground’s platform to meet enterprise‑scale requirements.
• Present to and influence senior decision‑makers, build consensus across diverse stakeholder groups, and guide complex decision‑making processes.
• Own long sales cycles from start to finish, including procurement, security, and compliance reviews, and negotiate pricing and contract terms for large, often multi‑year, multi‑center agreements.
• Build and manage a robust enterprise pipeline, maintain accurate CRM records, forecast revenue, and report on deal progress to leadership.
• Partner closely with product, onboarding, implementation, and customer success teams to ensure smooth deployment and adoption, and share enterprise customer feedback to inform product roadmap and packaging decisions.
• Help shape Playground’s enterprise go‑to‑market strategy, including ICP definition, pricing, packaging, and sales processes, and identify expansion and upsell 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 complex business problems and tie solutions to measurable business 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 skills, including contract negotiation and business case development.
• Mission‑Driven:
  Genuine interest in the early‑childhood education space and belief in technology’s ability to improve outcomes.

• OTE for this position is $175,000, subject to standard withholding and applicable taxes.
• Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process.

• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1,200/year education stipend
• Free lunch daily
• New Mac Book
• Collaborative and supportive work culture with a high level of autonomy and room for growth
• Help accelerate our mission to make excellent childcare accessible to all!

If you’re a hustler who’s excited to join a mission‑driven, early‑stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now.

This role is fully in‑office out of our LoDo, Denver office. Please make sure you are open to a fully in‑person role before applying.

Visit  to learn more about our journey and co‑founders Dan, Josh, and Sasha.

Seniority level
:
Mid‑Senior level
Employment type
:
Full‑time
Job function
:
Sales and Business Development