
Careers
Why Work at Playbook?
Join us on our mission to revolutionize traditional commercial real estate into thriving hubs of connection, wellness & productivity.

According to our staff
Rating 1-5
Recommendation Score
CEO Approval Rating
Our values & work culture



Pick up an oar.
Support your team. Eyes on the horizon. One direction.
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

Open Position
Description
Details





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
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
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
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
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
Onsite Customer Success Director
