Playground (tryplayground.com)
Playground (tryplayground.com) Career Growth & Development
Frequently Asked Questions
As a fast-growing company, career growth is naturally built into the experience at Playground. Team members have opportunities to grow vertically or move laterally based on their interests, strengths, and company needs.
Because of our stage, growth paths are highly individualized and less formalized than at larger companies. Progression is driven by impact, ownership, and readiness rather than rigid timelines. Managers work closely with team members to shape roles that expand in scope and responsibility as both the individual and the company grow.
We’ve promoted multiple team members into senior IC and first-time manager roles, and many have significantly expanded their responsibilities over time. We also intentionally launched an internal BizOps function as a leadership pipeline, offering exposure to cross-functional work and company-wide strategy.
At the same time, we deeply value individual contributors and provide pathways to grow in responsibility, scope, and compensation without requiring a move into management. We believe impact, rather than title, should drive growth.
Every employee at Playground receives a $1,200 annual learning stipend to invest in their growth and development. Team members are encouraged to use it to build skills aligned with their current role and long-term career goals, and we expect individuals to take ownership of their development.
Our founders also actively encourage employees to experiment with new tools and technologies, whether that’s purchasing and testing software, exploring AI tools, or building passion projects and internal tools using platforms like Lovable and other vibe-coding apps. There’s a strong emphasis on developing practical skills in automation and coding to increase leverage in your role and build durable, marketable capabilities.
In addition to self-directed learning, we provide skills-based training during onboarding and team-specific sessions led by managers or members of our operations team. These trainings are designed to strengthen core capabilities and continually raise the bar across the organization.
At Playground, learning is both self-directed and actively supported. We invest in our people and encourage them to experiment, build and grow.
Mentorship at Playground is primarily manager-driven. Managers work closely with their team members to provide regular feedback, coaching and support aligned with performance and growth goals.
Because we’re still a relatively young company, mentorship is largely informal and highly individualized rather than programmatic. We encourage team members to proactively seek guidance not only from their managers but also from more tenured peers across the organization.
As we grow, we continue to evolve how we formalize development support, but today coaching at Playground is hands-on, relationship-based, and grounded in real-time feedback and ownership.
Playground is a place where you truly get out what you put in.
There are meaningful opportunities to grow — from stretch projects and cross-functional initiatives to books around the office you can borrow and a dedicated learning stipend to use as you see fit. Leaders regularly offer special projects that give team members exposure to new skills and broader company context and share what they are learning with the team to pass knowledge and know-how around.
We’re a high-agency culture, so growth isn’t passive. The people who lean in, raise their hand, and take ownership of their development tend to grow immensely. For those who are proactive and ambitious, Playground can be an incredibly accelerating environment.
Playground (tryplayground.com) Employee Perspectives
What originally attracted you to Fortin, and what has kept you here as you’ve grown in your career?
I honestly didn’t know much about the child care industry before joining Playground, but I was immediately drawn to how fast-paced the company is. The product is constantly evolving, which keeps things interesting for both our customers and our team. Every day brings something new, so you’re always learning, adapting and picking up new skills.
Beyond the fast pace, the company culture and mentality has been a huge reason I’ve stayed. If you have a great idea, you’re encouraged to take ownership of it and see it through from start to finish. That’s not something you find everywhere. It’s incredibly rewarding to see your work have a direct impact on both the company and the customers we serve.
How have you grown or developed professionally during your time at Playground?
One of the biggest ways I’ve grown is by learning to balance a wide variety of responsibilities, many of which extend beyond my official role. At Playground, you’re not put into a box. If you’re willing to take initiative, dedicate yourself to something and prove yourself, the company recognizes that and gives you opportunities to grow.
I genuinely feel like I’ve learned more in the past year at Playground than I would have in several years at many other companies. A big part of that is because Playground has embraced my interests and given me opportunities to develop them, which has accelerated both my professional growth and my confidence.
Can you share a moment, project or experience that made you realize how much you’ve grown in your role?
One moment that really stood out was being asked to help train our first official new-hire cohort. I had the opportunity to travel to Denver to meet the new team members and lead product training, which was an incredibly rewarding experience.
It meant a lot to know that Playground trusted me to teach others about our product and represent the company in that way. Having both my managers and peers show that level of confidence in my product knowledge, especially this early in my career, was a huge milestone and really made me realize how much I had grown in my role.
Playground (tryplayground.com) Employee Reviews
What People Are Saying About Playground (tryplayground.com)
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Cross-Functional Experience: Work spans billing, enrollment/CRM, subsidies, food programs, communications, and reporting across admins, teachers, and families, creating broad problem exposure. Feedback suggests this breadth accelerates learning and collaboration across functions.
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Training & Education Access: An annual $1,200 education stipend (for courses, books, or conferences) and listed online learning perks materially support upskilling. This direct investment enables employees to pursue role‑aligned skills and longer‑term growth goals.
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Growth Culture: A “ship fast” ethos with frequent releases fosters tight feedback loops, ownership, and learning by doing. In‑person collaboration in NYC and Denver is described as enabling faster learning and stronger relationships.
Playground (tryplayground.com)'s Benefits
Provides continuing education stipend
Provides online course subscriptions
