Enterprise Account Executive

About the role

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.

Responsibilities

• 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

Requirements

• 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