Welcome back to Coffee Break, a Greenspace Series where we dive deep with one of our team members to uncover their personal stories, perspectives, and new ideas—or maybe even learn about some of their hidden talents that we never knew about.
Jason Frittaion
Jason Frittaion (”Like the word ‘Crayon’. Take out the ‘Cr’ and add a ‘Fritt’”) is the Director of Revenue Operations at Greenspace. He’s well known for his friendly competitive spirit, camp-counselor energy, and deep commitment to values-based leadership.
Raised in Mississauga, Ontario (or “the MDOT,” as he proudly calls it), Jason’s story starts in a uniquely expressive way: through his hands.
Jason grew up as a CODA, a Child of a Deaf Adult, and has been immersed in the Deaf community his entire life. His dad is hard of hearing, his grandparents were Deaf, and American Sign Language was woven into his childhood experience.
“You definitely get a different perspective. You’re straddling two worlds, being a hearing person within the Deaf community… It made me grow up a little quicker. Very early on, I was teaching my dad how to use a computer or interpreting at restaurants. You’re still the kid, but you also end up taking on the adult conversations at the same time.”
He credits this early experience with shaping his empathy, being tuned into the different ways people move through the world, and how important it is to make space for that.
“If you talk to my mom, she’d say I was the kid that saw every single charity commercial on TV and was like ‘we need to do something right now.’”
After university, that perspective took him across the world, where he I interned in the Philippines, supporting cooperatives run by persons with disabilities, many of whom were Deaf.
“I actually became a Filipino Sign Language interpreter while I was there and now I joke that I sign with a Filipino accent.”
From Econ Guy to Impact Architect
Jason studied business at Wilfrid Laurier University, originally intending to pursue accounting. But something shifted during his time on campus, sparked by clubs like Students Offering Support and experiences abroad.
“I started to take business and economics classes and I was like, oh I could become a chartered accountant and rule the world. But it was actually through Laurier, which is so focused on community and making a positive difference in people’s lives, where I got involved in community work, international travel, and volunteering, and I had this moment of clarity, like why wouldn’t I spend every day of my life trying to do something good?”
Through Students Offering Support, he became known around campus as “the econ guy,” leading packed tutoring sessions and raising over $70,000 in three years to fund development projects in Latin America. A trip to Costa Rica, where he stayed with a community who had lost their homes, left a lasting impression:
“I remember thinking there’s a whole world out there of people living different lives in different ways. It would be cushy to go work at one of the Big Four accounting firms, but I can’t ignore this.”
That pull led him to over a decade in nonprofit work, including time as a motivational speaker and a senior leader at jack.org, where he worked closely with young people to improve mental health support across Canada.
Bringing Metrics to the Mission
Jason joined Greenspace just over three years ago, drawn by the unique opportunity to combine his love of systems and strategy with a mission he deeply believes in.
“It brings together my interest in economics and systems-thinking with my passion for mental health. I’m inspired by how we bring measurement to something that’s often invisible, and how that measurement can change lives.”
As Director of Revenue Operations, Jason helps make sure Greenspace is not only growing, but doing so in a way that stays true to its mission. He was pleasantly surprised by how deeply the company’s social purpose is embedded in its work.
“I was surprised, in the best way, to see how deeply rooted the social mission is at Greenspace, even as a for-profit company. It reinforced that purpose can thrive across sectors.”
Trophy Belts, Sales Olympics, and Leadership Lessons
Ask anyone who’s worked with Jason and they’ll tell you: he brings a joyful sense of competition to everything. Whether it’s a gamified leaderboard or an office-wide mini Olympics, Jason believes play can be a powerful team building and leadership tool.
“At the end of the day, we’re just a bunch of humans getting together to try and do something. People often join an organization for the mission or the role, but they don’t stay for that reason. People stay because they enjoy each other, because they like the people that they work with. And so I think it’s always really important to treat each other like humans and ask: is there a more fun way to do this?”
With this in mind, he found a way to infuse his love of fun into his role, driven by his experience in cadets and motivational speaking, which helped him find his voice as a leader.
“I’ve always been very playful, but hadn’t found my leadership voice and confidence with public speaking. Cadets gave me the structure and the drive to develop that leadership voice as I grew in command and started to lead others. So that’s where I initially found it and then being a motivational speaker, it came with the territory.”
He credits several mentors with shaping his approach, especially those who led with humility, candor, and service.
“When I think of what kind of leader I want to be I often think back to Jeyas, the Director at the on campus restaurant at Laurier, because that man did whatever the team needed. If the restaurant was busy and we’re having trouble getting food out because we didn’t have enough dishes? He threw on the hair net, the scrubs, the apron, and he got in the dish pit, because that’s what was needed at the time. I think always being willing to dive in with your people is absolutely quintessential to good leadership.”
A Castle and a Bird
When asked about legacy and what it is he wants to leave behind, Jason shared how being a father of two has shifted his mindset:
“Ten years ago, I wanted my name on a building. Now? I just want to leave the world a bit better than I found it. I very much believe that we’re all standing on the shoulders of the giants of the past. So, I don’t actually think about my legacy. I’m just another drop in the bucket in that large pool of people.”
That ethos shows up in how he parents: with trust, autonomy, and a deep respect for his children’s unique journeys.
“Something that I got from my mom that I want to pass on to my kids is just a general sense of self autonomy and trust. Until we gave her a reason not to, she trusted us. That’s something that shaped me and that I want to pass on to my kids.”
He recently got a tattoo inspired by a book called On the Night You Were Born, that he used to read a lot to his son. It’s a castle with a bird flying above it.
“The castle strength and security, but also home. I want my kids to be the bird. Don’t be in the castle. Get out there. See the world. Live it. And just know that you can always come flying back.”
