In Conversation: Matt Lister of CloudAdvisors

Cloud Advisors

The In Conversation series is a chance for us to go deep with the people behind Victory Square Technologies’ twenty-plus portfolio companies. It’s an in-depth look inside what these companies do, and a chance to break down their approach to shifting paradigms in their respective industries.

The latest interview in the series is a conversation with Matt Lister, founder of CloudAdvisors. With their launch of Canada’s Employee Benefits Marketplace, Matt and his team are changing the game in the Insurance and Employee Benefits arenas.

This is a portion of a conversation between Matt and former CBC Radio host James Graham. It has been edited for clarity, space, and Zoom dropouts. The full conversation will be made available soon as part of Inside The Lab, the VST podcast series.


James Graham:  We’ll open with how I always open, which is to ask, what is CloudAdvisors and what’s your elevator pitch? How do you explain what you do to your parents?

Matt Lister: CloudAdvisors is Canada’s Employee Benefits marketplace. Simply put, we help employers get better benefits at a better cost. It’s really by connecting them with insights and access that they’ve never had before in that marketplace. We’ve organized hundreds of products and services from providers in the employee benefits and insurance industry. We’ve analyzed over ten thousand Canadian company plans so we can really tell employers exactly what a competitive employee benefits plan looks like. Then what we do is we automate the review and we automate recommendations, what we call solution matches, along with quotes, and we deliver everything digitally through secure portals to employers. So there’s a complete end-to-end simplified buying experience for employers on our platform.

James Graham: What differentiates you from the competition?

Matt Lister:  There are a few things that differentiate us. We’re agnostic and free of conflict of interest. We operate, platform, and partner with providers and advisors, but we don’t compete with them on any level. We don’t underwrite risk, we don’t issue policies or administer plans, provide advice, or sell insurance. What we do is provide the platform for all of that to happen. We’re also not competing with core legacy software, like third-party administrators, broker management, or even CRM. This allows us to be implemented in every situation where there’s a purchase decision being made. Some of our competition is going to be tied to a specific administrative platform or a specific insurance solution,  therefore, they’re going to be limited in their ability to become that true marketplace. The next thing I’d say is a deep understanding of the inner workings of this industry.  I myself come from the employee benefits industry working as an advisor for close to 10 years. I’m marrying that understanding of the fundamental principles of insurance with my co-founder’s understanding of the data and the technology needed to continue to innovate. So what we’re doing is building really true smart automation that can impact millions in the industry, not just additional software tools that will really only serve a few. Lastly, I’d say it’s what differentiates us from our competition is our focus on the employer experience.  I emphasize employer because we’re always having this employer versus employee nomenclature, but the whole of the insurance industry really exists to serve the consumer. Legacy members of the insurance industry fail to remember that but all this exists to serve employers, and our provider and advisor partners understand this. They understand that we’re building the next generation of infrastructure with their partnership that will allow providers and advisors to deliver really the best experience to employers and their people.

James Graham:  Could it be said that the next generation of infrastructure is the tool that CloudAdvisors is using to disrupt the insurance industry?

Matt Lister: In terms of how we’re disrupting the insurance industry, we focus on group insurance, which represents the vast majority of life and health premiums paid in Canada. There are really only two things that people care about when they’re purchasing insurance. What I should buy and what it should cost. So solving for that and providing the confidence to employers to say, I have the best plan is the best rate, it’s really all that matters. Our disruption comes from solving this problem faster, and really better than any traditional process. With our advisor partners on the platform, we can compare thousands of plans from across the marketplace to determine the right plan for any employer. By applying machine learning to the big data set that we have,  we can accomplish what would normally take a broker days or weeks, or if at all, in seconds. We actually do this every day. We do this practically with every employer on our platform and then we leverage the secure cloud to deliver those answers instantly to employers. So it’s really a speed advantage, but also the effectiveness of using the vast amount of marketplace data that we have access to compared to a single individual broker.

James Graham:  So the CloudAdvisors AI assistant really does give the client something of a leg up?

Matt Lister: Absolutely. When we’re presenting our AI assistant, who we call CA.L.E.B, to prospective advisor partners, we get a kind of a mixed reception. If they’re a young advisor in the industry, for the first time, they instantly love it because they get access to strategies and years of experience that would otherwise take ten or twelve years to accumulate. We get sort of a mixed reaction from our most experienced advisors, where they kind of say, “Well, this is what I can do with a client. And, you know, I’m not sure if I really need an assistant”. But that leg up, as you put it, where that really comes in is in three areas that we always highlight: speed, consistency, and scalability. So what would take that experienced advisor several hours of their time, several days or weeks of delay, we’re accomplishing for them in seconds. Speed is paramount in terms of delivering the most convenient experience, the simplest experience, and delivering those answers to employers. Then there’s consistency. An individual advisor typically looks after fifty to a hundred plus different clients and different employers. The reality is that not all clients get the attention that they deserve, or they need and the advisor tends to focus on the retention of key accounts or winning new business over proactive and thorough evaluation of all their clients. It’s just the nature of the limited hours in the day. So this creates a problem where businesses renew insurance policies year over year and are completely unaware of some of the issues that need to be addressed. The best advisors definitely want to do a better job, but they simply don’t have the time or resources, so the consistency suffers. The clients know that it’s a combination of the technology and the human expertise that’s providing that level of service. Then the last one is scalability. The industry is consolidating, a number of advisory firms, as well as insurance providers, are becoming larger. These problems that we talked about: speed and consistency, become worse when you lack the tools and ability. So our AI assistant, C.A.L.E.B, really gives the advisors the power to automate many aspects of their annual advisory model, ensuring that they can confidently grow their business well. Not just maintaining, but actually increasing the value to clients. So with the assistant on your side, that leg up is delivering faster, delivering for all clients consistently, and ultimately making sure that all of the gaps, the risks, the opportunities that exist for the client are being addressed.  That’s simply the experience that all employers deserve.

James Graham: In the time that I’ve known the CloudAdvisors team, the idea and the concept of transparency gets brought up a lot. How can optimizing b2b decision making through transparent communication affect a company’s bottom line?

Matt Lister: Transparency,  it’s a core value for us in our organization. It’s a key aspect that we think has been largely lacking from the insurance industry. Employers rely on their advisors to monitor their employee benefits program, but those reviews typically happen annually with the renewal. As we just talked about, employers don’t really know if there’s an issue. Problems may never be addressed, so costs can escalate quietly, or even larger risks, specifically to things like the drug plan, can mount and suddenly actually threaten the sustainability of an employee benefits plan. So you’re talking about the bottom line, I’d say that the decisions made or not made, don’t just affect the bottom line, but they actually affect employees and their family members’ access to health care. Where transparency comes into this is in obviously shining a light, or providing access to these insights, these problems, these gaps, risks, and opportunities that we talked about. One of the challenges that we identified is that advisors had traditionally been the guardians of information. Employers need to schedule a meeting in order to get a review, to get answers to get quotes. We need to create access for employers to really self-serve insights about their route. So consumers demand a level of access now to information especially when they’re making a purchase decision. This access also frees up our expert advisors to respond to demand better, and we want advisors not spending time setting up meetings so that they can then relay some of these fundamentals to employers. We should really be better responding to the demand to educate, advise, and ultimately making sales to employers that are better informed.

James Graham: Every entrepreneur has that lightbulb moment. They have that “aha” moment where they see the pain point that they know needs to be fixed. What was your “aha” moment?

Matt Lister:  The genesis of CloudAdvisors happened very early in my career, and I don’t think it would have happened if I delayed much further. Being an employee benefits advisor is a very lucrative position, it’s a very enjoyable role. But when I was working as an employee benefits advisor early on, I recognized my personal constraints. We’re asking the question, what would it look like to be an advisor in 10 years? Operating from some sort of digital platform was the assumption. Early in my career, I was fortunate to be mentored into the business by a very experienced advisor. I was fortunate to work with some very large employers. What we found, when we first started working with these employers and when we go into review the Employee Benefits Program, was that some of them have been quite honestly neglected by their current advisor. While that presented a lucrative opportunity for me to go in there and fix issues and sell new policies, I began to connect with the personal issues.  I think the “aha” moment really came when you start to see claims either being covered or claims not being covered, knowing that you had the solution for those employees.  I was also really struck by how the industry referred to groups or employers in the number of lives, instead of the number of people, I thought it was quite an impersonal sort of financial approach to a policy that’s really put in place to provide access to health care, to provide access to wellness, and provide access to retirement solutions for employees and their families that maybe otherwise wouldn’t get it somewhere else. When you start to see the opportunity to put in a better plan with better coverage, a better price to provide more access to employees, you start to look at,” how can I do this?” The constraint, as an individual is I’m eager to work with fifty to a hundred clients, as I mentioned, but through creating a digital offering that we can scale to all advisors in the country. This is about raising awareness of the competitive benefits, really across the entire marketplace. We know that small changes in a benefits plan, made a million times by different employers across the country, can create a massive impact on working Canadians. We’re arming our advisor partners with the ability to efficiently reach employers.

James Graham: Talk about your team and how they have contributed to the success of CloudAdvisors.

Matt Lister: There are a few quotes in business that have been guiding principles for us. One that I picked up from our business coaches a long time ago was “people don’t exist to serve a business, but the business exists to serve its people.” A related one that I think is Richard Branson is “take care of your people and your people will take care of your business.” When you’re first starting out, it’s only a couple of you, and you’re not paying yourselves. You’re working on this vision, you’re doing everything, and you have to be doing everything. But then as you sort of innovate and develop a process,  you look to hire talented people that can not just take on that process from you but can really make it their own and have their own unique ideas. What we’ve really benefited from, and I’m sure a lot of organizations have benefited from, is hiring really talented people and giving them a level of autonomy and ability to innovate within their own roles. Some amazing ideas have come out of that. We tout CloudAdvisors as a meritocracy. Meaning that the best ideas or the ideas with the most merit are really the ideas that should be raised to the top. So we meet as a team once a week and we really work things through, to an outside observer, probably to a level of frustration. But it’s in that creative destruction that we come up with some really great ideas. My co-founder, Rahul, has put a huge emphasis on culture from day one and working together. We’ve been able to maintain that cohesiveness in our virtual environment through our daily huddles, and through our various weekly meeting cadence. We’ve also spent a significant amount of time and resources on recruitment and recognizing that that’s not just a big business problem, but that’s an any-size business problem. You need to hire people that are smarter than you, that are more talented than you, and specifically bring a level of cognitive diversity to the team. So Rahul’s been fundamental in formalizing partnerships with universities like the University of British Columbia, and the Sauder School of Business to formalize those pipelines and establish a presence there for future talent acquisition. In the last year, we’ve seen some absolutely amazing individuals come through there and I’ve been fortunate enough to work with them and to have them join our team.

James Graham:  How are CloudAdvisors driving growth in what is seemingly a competitive market?

Matt Lister: Yeah, it’s absolutely a competitive market. The insurance industry is one that really hasn’t changed materially in the last hundred years or three hundred years, depending on who you ask. The last hundred years being the group insurance market in Canada. With the advent of available technologies and the consolidation happening in the industry, this is a rapidly growing market. Insurance itself is growing year over year in terms of the number of covered Canadians as well as the premiums that they’re paying. So it’s really been with a clear mission that CloudAdvisors has stayed focused, and sometimes what we refer to as staying within our own lane, on what it is we’re trying to accomplish. That is to democratize access to healthcare and to make insurance better for everyone. By democratization, we go back to that transparency and that access to not only the programs that employees and their families rely on but also the access to information and decision making that employers rely on to put those programs in place and make the insurance better for everyone. We talked about the process of purchasing insurance being as simple as possible, and being able to solve the question, what should I buy? And what should it cost? The easiest way that we can solve that question, that’s gonna earn us the attention of advisors and employers that are making those purchase decisions on coverage in the marketplace.

I would also add that driving growth in a rapidly growing market involves us listening and prioritizing. So we spend a great deal of time listening to customers, listening to different stakeholders, whether they’re provider partners or advisor partners, as well as directly from the employers that experience our software through our advisors. In prioritizing feedback, whether it’s new features or improved user experience, or ultimately getting ideas on completely new workflows and ways that we can further simplify the process, it does go back to the people. Driving growth, the only way we can do it, is to scale our own organization and that’s done through recruiting amazing people to help us achieve those goals.

James Graham:  So we’ve covered a bit of history, we’ve covered the Now. Where do you see CloudAdvisors in the next five years, and how are you guys getting there?

Matt Lister: The vision for CloudAdvisors is a global marketplace for employers powered by artificial intelligence. If I unpack that vision a little bit for you, there are three aspects that would stand out. One is a global aspect. Our Canadian solution today, impacting the group insurance market in Canada, which is just over $80 billion dollars a year in premiums. But certainly, within the next five years, our ambition is to expand into other markets. We’ve had promising development with partners that have a presence in the United States, as well as global benefits partners that have a similar presence in other markets around the world. In terms of the marketplace itself, while we’re focused on employee benefits, there exists an opportunity in other programs and other plans that employers need to interact with and have the same challenges and complexity that are faced in the employee benefits world. We’ve recently launched our retirement savings benchmarking, which is an aspect of the group retirement coverage, where now employers can look at RRSPs, they can look at pension plans. That’s a whole new market for us to help address and bring that decision-making process down to a much simpler lens. Then expanding from there into wellness, compensation, and either even other lines of insurance that employers need to address. The last part of the vision is really powered by artificial intelligence. So that really speaks to the technology and while we’re using machine learning, and big data, and cloud infrastructure today, the possibilities for artificial intelligence to truly meaningfully impact our business are still somewhat unknown. We see the potential for the growth in our technology, to not just help with decision making, but to help with predictive analytics. To really help insurers even understand the needs of employers and help employers understand risks that they may not even have in their business today. Things that are being identified in the patterns of the data, so artificial intelligence for us represents sort of the ultimate in efficiency and effectiveness. That, paired with your expert advisors, and the marketplace should again achieve the simplest experience for employers.


Matt Lister is one of the co-founders of CloudAdvisors.

James Graham is still very tall and internationally known.

Related Posts

Victory Square

x