Enterprise Account Executive

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 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 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 $285,000, 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 (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed salary is a guideline, and the salary for this role may be modified.

Why Join Playground

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• Free lunch daily

• New Macbook

• 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!

How to Apply

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. The Playground Team is fully in-office in Union Square, NYC and LoDo, Denver offices. Please make sure you are open to a fully in-person role before applying.