Ryan J. Jennings is Founder & CEO of Wealthletics, bringing 25 years of corporate and financial planning experience with a focus on the people behind the money, not just the investments. A three-time company co-founder and technology entrepreneur, he’s applied AI to organizational change for over five years. He is a past United Way of Calgary Board Member and served as Volunteer President and Board Chair of Alzheimer’s Calgary and Dementia Network Calgary for the last 12 years. He is passionate about helping teams and organizations build measurable, meaningful financial wellness programs that strengthen both their people and their bottom line.
We are delighted to be partnering with Wealthletics for our Calgary Summit this year and that Ryan will be running a fantastic workshop: Financial (Un)wellness: Do you know the amount it’s costing your organization today?
We caught up with him to see how he’s feeling in the run up to the summit:
Hi Ryan, we are thrilled that you are joining us at the Wellbeing at Work Summit in Calgary this October. Our first and most important question is, how are you doing today?
I’m doing great, thank you! Soaking up the last of the summer weather while riding the “back-to-school” energy of everyone shifting back into productivity mode…
As a leader based in the region, what are the main challenges you are facing when it comes to employee wellbeing and mental health?
Financial stress and anxiety are the dominant theme right now. The lingering aftereffects of the pandemic, political and trade tensions, across-the-board price inflation, rising interest rates, and an increasingly complex and fragmented financial services ecosystem. One of our guiding principles, from both a partner and a user perspective, is to turn these stressors into opportunities to help people make their financial lives better.
Getting people into action is the real feat. Knowing better is one thing; doing better is another; doing it consistently is a third layer entirely. It takes very human skills like initiative, motivation, discipline, and personal growth, all of which stress erodes fast.
Much of our work at Wealthletics is about meeting people exactly where they are. We focus on the human being first, on their beliefs and mindset, and on the intersection of money and psychology. That is often where the real shift happens, beyond just the technical side of financial planning.
What strategies have you seen developing over the past 6 months, both internally and externally, that are moving the dial on wellbeing in the workplace?
The pandemic put a much-needed spotlight on mental health and reduced the stigma around asking for support. We are still living through the post-pandemic recalibration, and the best-performing organizations are addressing it with more flexible hours, less limited time off, profit-sharing and performance incentives, greater mental health resources and wellness stipends.
We are seeing corporate wellness platforms mature into something far more holistic, supporting employees across many more dimensions of their lives, not just one or two.
Why is employee wellbeing so important to you personally?
Anyone who has navigated stress, trauma, mental health challenges, or watched someone they love to do so, knows how frustrating that journey can be. Despair, low motivation, anxiety, and depression can show up throughout it.
I am driven by seeing people feel joyful and empowered, and high-performing teams excelling at their mission. One person can only do so much alone, but Wealthletics is built to make that empowerment accessible at scale. Investing in yourself is one of the greatest investments you can make, and it multiplies when you do it in service of helping others and those you love. When an employer makes that easier, it becomes a genuine, mutual relationship of care.
What impact is AI having in your organization and how are you managing that?
AI sits at the heart of how we run the company. It helps us operate more efficiently internally while opening access to guidance and coaching that has historically been available mainly to affluent people or those with top-tier advisors already in place.
We are an efficient and effective team with big ideas, and AI helps us bring those ideas to market more quickly. Our north star is simple: help people build a stronger relationship with their finances, and for those who wish to use AI safely and effectively it can serve as an accelerant.
We also recognize that adoption is not uniform. Some people are quick to embrace AI, while others are more hesitant. That is why we built a choose-your-own-adventure type experience, where people can work independently, receive guidance from our agent, use an AI tool of their choice, or work hand in hand with a real person throughout the process to make their financial life better.
Other than AI, are there any challenges that you are seeing for the first time and how are you addressing them?
Collaboration is still a genuine challenge in the modern workplace. How teams work together, how individuals stay connected, and how those dynamics shape the employee experience all matter. We believe in balancing human connection with technology, using collaborative meetings alongside modern tools. The “always-on” effect is real, especially with flexible schedules and teams working across time zones. People can feel pressure to stay available well beyond traditional working hours, which makes it harder to switch off and maintain healthy boundaries.
AI can increase output, but it can also raise the risk of burnout, especially when high performers feel pressure to keep pushing beyond healthy limits. People are also still cautious about how AI uses personal information, particularly when it comes to their finances. That is why our approach provides useful guidance without relying on personally sensitive financial data or creating concern that it could be connected back to an employer.
What areas do you think employers should be focused on over the next 12 months?
The employee experience is central to retention. Organizations invest heavily in attracting new talent, but there is an equally important opportunity to support the people who have already chosen to stay and are committed to helping build the organization’s future.
Financial wellbeing is one practical place to start. When people are worried about money, it can affect their focus, confidence, ability to plan, and capacity to bring their best selves to work. Our market research shows that 51% of Canadian workers spend at least 15 minutes of their workday thinking about their finances, up from 45% the year before. Nearly one in four say financial stress has affected their performance at work.
That creates a real opportunity for employers to make retention efforts more meaningful and measurable. Canadian employee financial stress is estimated to cost businesses $69.5 billion in lost productivity each year, making financial wellbeing both a human issue and a business one. Giving people access to tools, guidance, and support that help them build financial confidence can strengthen their day-to-day wellbeing and their connection to the organization.
Retention is not about convincing people to stay. It is about creating the conditions where people can thrive, feel supported, and see a future with the organization.
Do you feel that investment in employee wellbeing in the region is increasing or decreasing and is that a direct reflection on HR leaders’ increasing ability to demonstrate effective returns of their strategies to leadership?
It is a mixed picture. Some sectors are investing more deeply in wellbeing, while others are navigating competing pressures. Across industries, however, employee expectations around financial pressure, mental health, caregiving, flexibility, and support are making wellbeing a more important part of retention and total rewards.
There is also a visibility gap. Employees currently rate their financial wellness at 55%, while employers estimate it at 71%. Better metrics help close that gap and show where support is most needed.
We love seeing partners deepen their perceived investment in the programs they already offer. For example, six in 10 Canadian workers do not fully understand their workplace retirement or savings plan. Targeted education and milestone tracking can help employees use those benefits with more confidence while giving employers a clearer view of impact.
How has your organisation been leading the way?
Honestly, what has stayed with us is how quietly people carry financial stress. It reaches far beyond a bank balance. It can affect sleep, relationships, confidence, focus at work, and the hope people have for their future.
That is why, for us, the solution has never been just about finances. It is about the person behind the financial situation. We are building something that meets people where they are, whether that means a quick insight, one manageable next step, or time with a real person who can listen without judgment and help them work through an important decision or turn felt chaos into calm clarity.
We want to help people move from financial overwhelm or avoidance to clear, capable, and a feeling of being more in control. If someone can better understand what matters to them, take a meaningful next step, and rebuild trust in themselves, that is real progress.
At the end of the day, Wealthletics uses technology to make support more accessible while keeping the experience human. With cost of living is now the top financial stressor for 63% of Canadian workers, we know this support is needed now more than ever.
Ryan will be speaking in Calgary this October as part of our Wellbeing at Work Summit Canada which take place in both Toronto and Calgary. Click the links below to find out more and book your tickets:
Toronto Summit October 20: Find out more and Book Your Toronto Tickets Here
Calgary Summit October 22: Find out more and Book Your Calgary Tickets Here
