Profile
Massimo Ianniruberto founded Cloven as a consulting business until he saw the potential to turn what they were building for individual clients into products that could help many more. This shift in thinking became the driving force behind how he built the company.
Launching Cloven’s second product was the moment that proved his instinct right. The first product showed what was possible, but the second gave him something more lasting. “It proved that our initial success wasn’t an accident and that we had a team capable of taking another idea from concept to launch,” Ianniruberto says. More than the launch itself, he is proud of what it revealed about the business he and his team were building together.
Staying focused on Cloven is its own challenge in an industry where new technology, particularly AI, is constantly competing for attention. “I try to bring every decision back to our clients,” Ianniruberto says. “What problem are we solving, and will this make a meaningful difference for them? That helps us focus our time and energy where they matter most.”
His confidence in that team carries into how he leads. He gives his team the space to do what they do best and backs it with clear expectations, guardrails, and his own availability when support is needed. “People do their best work in an environment that allows them to grow,” he says.
Ianniruberto relies on listening as much as direction. “Understanding what someone actually needs gives us a much better starting point than assuming we already know the answer,” he says. He also trusts the strengths of the people around him rather than trying to do everything himself, an approach he carries into his own career by staying curious, taking responsibility, and creating room to keep developing.
Trust and relationships are just as central to how he works with clients. Ianniruberto maintains a personable demeanour, remaining genuinely interested in people and honest about what the business can deliver. “I’ve been honest about what I know and what I still have to learn,” he says.
“Approaching a conversation as a student often creates space for a more open exchange.” Being willing to ask questions, he adds, has helped him build relationships, learn faster, and bring a fresh perspective without pretending to have all the answers.
Mentorship has also shaped his decision-making. It has given him perspective on when to try something new and when to follow a path that is already proven and helped him move forward with more confidence and less overthinking.
The Rising Star nomination has already left its mark on how Ianniruberto works. “The recognition has made me even more focused on working closely with clients,” he says. “It’s encouraging to have the work recognized, and it reinforces my motivation to keep earning their trust and understanding where we can help.” He wants to stay close to the people using Cloven’s products and let their needs guide what they get to build next.
2255B Queen Street East, Toronto, ON, M4E1G3
613 927 1230
mianniruberto@bluroot.ca
linkedin.com/in/massimoianniruberto
cloven.ca
Massimo Ianniruberto
Co-Founder
Cloven
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Bio
Milestones
2014–present
2023–present
2024
2025
2023–2024
Co-founded Bluroot as a technology consulting firm focused on solving complex business challenges
2014–present
Helped launch and grow Cloven, a CRM built for Canadian financial advisors
2023–present
Bluroot recognized by The Globe and Mail as a Top Growing Company in Canada
2024
Cloven named WealthTech Service Provider of the Year at the WP Awards for Excellence
2025
Senior Wealth Advisor at Harris Group Private Wealth Management
Regional President’s Cup Award
2023–2024
Milestones
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Jesse Harris,
Harris Group Private Wealth Management
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Jesse Harris,
Harris Group Private Wealth ManagemenTt
Harris’s path to financial planning began while studying to become a doctor, when he realized his passion for helping people could be fulfilled through financial services. Originally from Mission, BC, he moved to Victoria to play hockey in high school and stayed to complete university. He now lives on Vancouver Island with his wife, Cindy, and their two children. Outside of work, Harris continues to enjoy hockey, coaching his children, and celebrating milestones with his clients.
Massimo Ianniruberto