Enterprise Account Executive

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 $285000 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.

What We Do

For too long child care programs have been stuck with clunky tools and manual processes falling behind while other industries get all the high-tech toys.Playground is flipping the script. Playground is a proven platform for child care providers to streamline their operations reclaim their time and get back to the joy of teaching and caring. Our all-in-one child care management software manages billing attendance registration and enrollment communication paperwork payroll and more.

Why Work With Us

At Playground we’re a mission-driven high-growth startup where collaboration creativity and entrepreneurial thinking fuel everything we do. We act like owners take initiative and make smart decisions independently every day. Join us to make an impact grow fast and be part of a team that truly values your ideas energy and drive.

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