Enterprise Account Executive

What You’ll Do

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

What You Need

• 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

Compensation & Benefits

• OTE: $285,000
• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1200/year education stipend
• Free lunch daily
• New Macbook