Enterprise Account Executive

Denver, United StatesOn-site

Responsibilities

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

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.
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: 5+ years closing complex enterprise SaaS deals with long sales cycles and multiple stakeholders (vertical SaaS

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 - OTE for this
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.

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

ABOUT PLAYGROUND 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.
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.
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.
This role is fully in-office in Union Square, NYC or LoDo, Denver.