Continuously strengthening our insurance practice means introducing innovative solutions and expanding the Bridgewell team to better serve our clients. For us, insurance is about more than products—it’s about helping people live better, longer lives with greater peace of mind. That belief has been central to Bridgewell’s approach since the firm was founded. By bringing together experienced professionals who share this perspective, we help our clients build financial plans that support their long-term goals.
One of those professionals is Senior Advisor Cheryl Siskind Solomon, an insurance industry veteran who has been a part of the Bridgewell team since the beginning. Cheryl brings a unique perspective to our firm, working closely with us while also leading Get a WRAP. a specialized offering designed to help seniors manage the rising costs of catastrophic care as they age. In our latest Meet the Bridgewell Team Profile, Cheryl reflects on her early career in the insurance industry, shares why Bridgewell’s founding vision—centered on wellness and community giving—aligned with her values, and offers a glimpse into her life outside of work.
Can you provide some details about your professional background?
I started my career in the insurance world working for two successful insurance advisors. Within two years, with their support and encouragement, I was fully licensed and starting to build my own career. I had exposure to two different ways of providing insurance solutions to my clients, both technical and client facing, and I learned from both. My years with them helped me formulate my own path in the industry. Along the way, I met [Bridgewell Financial partners] Chad [Tranter], Michael [Wortsman], Mike [Tranter], Graeme [Martin] and [Bridgewell Senior Advisor] Judy [Tranter] and other members of our team. We worked together for many years at another firm, building the business and working to serve clients.
What appealed to you about joining the Bridgewell team?
I was drawn to Bridgewell for its vision of financial, physical and community wellness—and the opportunity to be part of a truly collaborative team. The values that Bridgewell stands for align deeply with who I am, both personally and professionally.
Over the years, working alongside the partners, it became clear that their vision is unlike anything I had experienced in previous organizations. Here, teamwork isn’t just encouraged—it’s expected, without question. That environment is incredibly meaningful to me, as it allows me to bring real, lasting value to our clients. At the core of it all is a strong sense of mutual respect, which defines how we work together and how we serve the clients who trust us with their planning.
How do you collaborate with the Bridgewell team?
Throughout my career, I started out working closely with families and over time expanded into corporate planning. What I really value now is how we work together at Bridgewell—it’s very collaborative.
We share ideas, talk through different strategies, and build solutions together. Whether it’s with the admin team or the partners, it’s always a two-way conversation. That exchange of perspectives makes a real difference in how we support our clients.
What do you think is unique about Bridgewell’s service experience and culture, in particular the insurance solutions offered through Get a WRAP?
What’s unique about Bridgewell is that it lets us focus on what matters most—our clients and the conversations that truly make a difference—while being fully supported by an incredible service team. For me, that shows up through WRAP. I’ve spent more than 25 years helping clients plan for the cost of care as they age, and it’s still one of the most overlooked risks out there.
At Bridgewell, we don’t avoid that conversation—we lead it. We help clients understand the potential financial impact and, more importantly, that there is a way to insure against that risk. It’s about protecting their dignity, their assets and their families—and that’s what makes what we do so meaningful.
What do you like to do away from the office?
My husband and I live an active lifestyle. We moved to our cottage in Parry Sound a few years ago and embrace outdoors activities in all seasons. We’re lucky to be part of a wonderful community of active friends. Together we spend time biking, walking, dining, cooking and enjoying the local culture. Family is a big part of our life. We’re incredibly proud of our adult kids and now watching our teenage grandchildren find their own direction is really special.
Marlie, our Bernese Mountain dog fills our home with undeniable cuteness and cuddles.
We still travel back and forth to Toronto, and we’re in the process of building a garden suite so I can work in the city, stay connected to our wonderful family and dear friends and enjoy what Toronto has to offer.
The Bridgewell team
For assistance with your wealth and financial planning, insurance or group benefits planning needs, contact a member of our team today.
