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 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.
Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.
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