Playground (tryplayground.com)

HQ
New York, New York, USA
Total Offices: 2
60 Total Employees
Year Founded: 2021

What It's Like to Work at Playground (tryplayground.com)

Updated on February 25, 2026

Frequently Asked Questions

Job Satisfaction

At Playground, we’re intentional about creating an environment where people feel heard and valued.

We run biannual anonymous employee feedback surveys to gather candid feedback and share action plans with the team. 

Leadership prioritizes transparency through twice-monthly founder-led all-hands, a weekly CEO update on company performance and priorities, and open “Ask Me Anything” office hours. 

Recognition is embedded in our culture, with regular peer and manager shoutouts, quarterly culture awards, and celebrations of team milestones and anniversaries.

We continuously look for ways to improve the employee experience and ensure everyone feels connected to our mission and impact.

Willingness to Recommend

Yes! The vast majority of our team members love working at Playground and would recommend it to friends and colleagues.

In our most recent staff survey, 15 out of 34 employees rated their likelihood to recommend Playground as a 9 or 10 out of 10. Another 13 rated their likelihood as an 8 out of 10. 

Employees consistently point to our mission-driven focus and positive social impact, transparent and caring leadership team, incredible product, and high-performing yet fun culture as the reasons they enjoy being here.

General Market Perception

Playground is known for having a supportive, collaborative team environment where ideas are valued and employees are encouraged to take ownership of meaningful projects.

We offer competitive compensation, including equity, comprehensive health benefits, three weeks of PTO, a $1,200 annual education stipend and free daily lunches.

We also prioritize sustainable work rhythms. Our team works in-office from 9–6, with a full hour lunch break built into the day — and covered by the company — to encourage real downtime and connection with team mates.

Above all, Playground is recognized for having deeply empathetic, caring leaders who are invested in both the professional growth and well-being of the team.

Tradeoffs

Playground is a fully in-person company. Team members work together in the office each day, so those who strongly prefer remote or hybrid flexibility may find that challenging.

We’re also a fast-growing startup, which means there’s a high degree of change and ambiguity. We value ownership and high agency — people here are expected to take initiative, move quickly and help create structure rather than wait for it. Those who prefer very defined processes and steady, predictable environments may find that less appealing.

For the right person, though, these tradeoffs come with meaningful impact, close collaboration and the opportunity to help shape a company in motion.

Job Satisfaction
Willingness to Recommend
General Market Perception
Tradeoffs

Playground is a place where people care deeply — about the mission, about the product and about each other.

Because we’re still growing, employees have real ownership and visibility into their impact. Work doesn’t get lost in layers — ideas can quickly turn into shipped features, new initiatives or meaningful improvements. That level of access and accountability shapes how people experience working here.

We’re intentional about building a values-driven culture that balances high performance with genuine connection. We celebrate wins, learn openly from challenges and aim to create an environment where ambitious, mission-aligned people can do the best work of their careers.

Playground (tryplayground.com) Employee Reviews

Playground has been a game-changer for me. Every day, I get to work alongside mission-driven people who care deeply about making a difference, and together we build something meaningful for kids and educators. I love that my ideas are valued, that I have ownership over my projects, and that collaboration is at the heart of everything we do. Being part of a team that shares a common purpose makes the work energizing, inspiring, and deeply rewarding. If you want your work to matter and to grow alongside people who are passionate, curious, and committed, Playground is the place to be.

Talia Kirshenbaum
Talia Kirshenbaum, Talent Lead and Founding Recruiter
Talia Kirshenbaum, Talent Lead and Founding Recruiter

Playground strikes a rare balance of being fast-moving and deeply supportive. The culture encourages curiosity, ownership, and empathy - for both our customers and each other - while giving me the opportunity to build meaningful relationships around a product that truly makes a difference for child care providers and the families (like mine!) that they serve.

Jess Fleming
Jess Fleming, Account Executive
Jess Fleming, Account Executive

I’ve spent my career in mission-driven startups, and Playground stands out for the level of care, empathy and trust with which our founders lead. We’re building a product we truly believe in — one that meaningfully outperforms alternatives in solving our customers’ needs — while also scaling a high-growth, high-performing company. There’s genuine care for the people here, and in turn, our team deeply cares about the providers we serve and the mission we’re working toward.

Aileen Gray
Aileen Gray, Biz Ops Lead
Aileen Gray, Biz Ops Lead