Founders Story: Matt Lister

This week, we wanted to spotlight our Co-Founder and CEO, Matt Lister!

A little bit about Matt:

Matt is a dad joke connoisseur, father to 1 year old Brodie, and dog-dad to goldendoodle Branson with his wife Kailey. Outside of work, Matt enjoys trail running, all things Star Wars, and spending quality time with his family.


Matt Lister’s journey began after graduating from the University of British Columbia with a Bachelor of Human Kinetics, and a minor in Commerce. Out of school Matt was mentored in the insurance industry as an Employee Benefits Advisor through Davis Benefits & Pensions. After 8 years, Matt left advising to pursue insurtech full time; co-founding CloudAdvisors, and serving as CEO to a company he is incredibly proud of today.

updated matt headshot

Matt, tell us about the origin of CloudAdvisors.

“The idea for CloudAdvisors was born about 10 years ago. As an advisor I met a number of business owners that could benefit from our advice, and I saw first-hand the impact better benefits had on their employees and their families. The question that always lingered for me was how to impact as many employers as possible, not just my block of clients. I started to question what being an advisor would look like in 10 years, and I pictured a paperless, data-connected expert capable of helping organizations across the country. 


When I realized this didn’t exist yet, I knew it was something I wanted to build. I reached out to my long-time friend Rahul Rao, who at the time was CEO of Trans Oceanic Intelligence Services (TOIS). TOIS was doing some amazing work with trucking companies. Rahul showed me how he used technology to track and regulate logistics and driver behaviour in Asia. Together, we brainstormed our ideas to automate the benefits industry.

Unfortunately, our ideas had development costs that were a non-starter for a single advisory firm. It was around this time that I met Faizal Mitha, who was heading down a similar path with his own firm. The three of us put together the framework of what would become a platform to revolutionize the industry. As the business progressed, we partnered with TOIS and their development team. As late nights continued into full weekends, the business expanded and we monopolized all of TOIS’s resources to build the first version of the platform.


In our first few years, we really struggled with the founder’s dilemma: how can we leave our lucrative day jobs to pursue our new company. Through the support of our original investors, our friends, family, hard work, and determination, we got the company off the ground.  Faizal had the opportunity to evolve his career to another level with HUB International. Rahul merged TOIS with CloudAdvisors. And I transitioned from an advisor at Davis to full-time CEO at CloudAdvisors.


Fast forward to today. Seeing our dreams and aspirations of a new industry developed on Friday nights, now a reality has been a tremendous accomplishment for us. What allowed us to keep the dream alive was a lot of patience. Both on our parts and that of our amazing support systems.”

Who were the people who have been the most helpful in getting you to where you are today?

“To be quite honest, it’s hard for me to just pick one or two. My dad is a real inspiration to me. He studied engineering and was top of his class in his MBA at Western University. Retired now, he had a very successful career in business. He always prioritized family, finding balance and being there for us in our school and sports. It’s something I think about a lot with my one year-old son today. 


Kirk Davis was my mentor in the insurance industry. We met on the golf course one day, and he sold me on the employee benefits industry. Through his mentorship he gave me the ultimate freedom and autonomy to learn what I needed. I earned my Certified Employee Benefits Specialist designation, and worked with a number of amazing clients. The autonomy and freedom we have here at CloudAdvisors was inspired by my time with Kirk. 


I have to mention both Rahul and Faizal, without whom we wouldn’t have CloudAdvisors today. Both their business sense, and character make them incredible partners, human beings, and people I am proud to call friends. 


I also have to mention my amazing wife Kailey. She has always kept me grounded. She’s helped me in countless ways. Most importantly, in reminding me to not take life too seriously. Even in those early years, when I was working 7 days a week on a dream. She’s helped me to appreciate the balance in finding time for health and laughter. And to remember all the wonderful moments along the way. Not just what’s to come next!”

Where do you see CloudAdvisors in 5 years?

“This question really excites me. In 5 years time I see CloudAdvisors as the digital marketplace powered by artificial intelligence, for employers to connect with advisors, providers, and solutions. We want to break down multiple markets and expand globally. Both advancing the accessibility of the marketplace, and the technology to provide more value to all employers looking to support their people.


Most business owners don’t want to talk about insurance. They want to build their business and ensure that competitive solutions are in place to take care of their employees. We want to make purchasing insurance as short and sweet as possible. We want our AI and marketplace to bring information to the surface instantly. After all, in any complex purchase it’s the right information at the right time that provides confidence and understanding to make the right decision.


It’s important to acknowledge AI is still just a tool. Our hope is that it will augment the best advisors, evolve their approach, and free their time to re-invest in the best experiences for employers.”

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