Careers

Careers

Why Work at Playbook?

Join us on our mission to revolutionize traditional commercial real estate into thriving hubs of connection, wellness & productivity.

Work

According to our staff

Rating 1-5

+27.8%
4.6%

Recommendation Score

+35.29%
92%

CEO Approval Rating

+28%
96%

Our values & work culture

Pick up an oar.
Hone your craft.
Send it.

We Value
Our Team Members

Medical

Free Employee-only medical coverage under two of our four medical plans

Family Coverage

Company subsidized medical, dental and vision coverage for you and your dependents (spouse, domestic partner, children). Plus options to purchase voluntary LTD coverage, additional life insurance, etc…

Disability

Free Employer Paid. Short-Term Disability and FREE $50K Life & AD&D Insurance

PTO

Our Host Team members receive 3 weeks of PTO and 6 company holidays. They are also are off when the building where they work is closed

We Value
Matt Reilly
Oscar Rivera
Stefanie Kassab
Chad Kowaleski
Lauren Gremizzi

What our Team
is saying.

I've been here for three years, and what keeps me excited is the autonomy we have to experiment with new technologies. Last quarter, I proposed migrating to React Server Components, and the team was fully supportive. We're not just using the latest tech—we're actually solving real problems with it.

Matt Reilly

Matt Reilly

VP Engineering

The on-call rotation here is actually manageable, which sounds crazy but it's true. We've invested heavily in monitoring and automation, so when issues do come up, we have the tools to fix them quickly. Plus, the team actually values work-life balance—it's not just a buzzword.

Oscar Rivera

Oscar Rivera

Director of Engagement Marketing

The design team here is small but mighty. We're embedded with engineering from day one, which means our designs actually get built the way we intended. No more 'lost in translation' moments. Plus, everyone genuinely cares about the user experience.

Stefanie Kassab

Stefanie Kassab

Sr. Director, People

"Working at Playbook has been a transformative chapter in my career. The leadership team genuinely supports growth, and I’ve had chances to learn new skills and take on exciting challenges every month. There’s always room to experiment and innovate here."

Chad Kowaleski

Chad Kowaleski

Software Engineer

“The people here make every work-day something special. I feel like part of a community that truly cares about delivering amazing experiences for clients and building each other up. Teamwork and collaboration aren’t just buzzwords—they’re how we operate!”

Lauren Gremizzi

Lauren Gremizzi

Onsite Customer Success Director

Ready to increase your asset value?

Join the Playbook team.

Where work works
Your office building has more to give.
Office reimagined.
Where work works
Your office building has more to give.
Office reimagined.
Where work works
Your office building has more to give.
Office reimagined.
Where work works
Your office building has more to give.
Office reimagined.
Where work works
Your office building has more to give.
Office reimagined.
Where work works
Your office building has more to give.
Office reimagined.