Sheldon is passionate about helping people, whether it’s family, friends, neighbours, or his wider community. With the support of his Portfolio Management team, clients have the expertise needed to build the right investment mix. As a Wealth Advisor and Family Enterprise Advisor with over 3 decades of industry experience, Sheldon helps Saskatchewan-based families prepare for retirement, protect generational wealth, and transition their businesses or farms with clarity and confidence.
Growing up on the farm has taught him the value of hard work, dedication, integrity, and principles that he carries into every client relationship. Sheldon believes trust is earned, and he is committed to showing up with perseverance and authenticity in everything he does.
At Optimize Wealth Management, his focus is on guiding individuals through the bigger picture: preparing for retirement, staying comfortably retired, and navigating important financial decisions with clarity and confidence.
Within the last 30 years of being in the investment business, Sheldon spent the last 8 years as a Portfolio Manager (PM). He also holds the Certified Financial Planner (CFP), and the Certified Investment Manager (CIM) designations. He is also a Family Enterprise Advisor (FEA), which equips him to help families transition their businesses and farms to the next generation.
For Sheldon, it's not just about numbers, it's about protecting wealth, strengthening family ties, and ensuring that legacies last for generations.
When Sheldon is not working, you'll find him playing hockey, baseball, or helping his community through his Kiwanis service club.
Your partner in personalized, full-service wealth management
Your ally in the pursuit of financial freedom
We go beyond just managing money. The Gray Team optimizes your financial journey through modern technology and sophisticated expertise, providing dynamic, personalized strategies. We’re dedicated to connecting you with holistic, transparent advice that aligns with your unique goals.
Meet the team
Sheldon Gray, FEA, CFP®, CIM®
Investment Advisor
- Email: sheldon.gray@owm.com
- Phone: (306) 520-8042
Mathew Cain, CIM®
Portfolio Manager
Mathew Cain is a Portfolio Manager at Optimize who partners with advisors, wealth planners, and clients to build tailored portfolios. He provides clarity on Optimize’s investment approach, personalized advice, and timely economic updates.
His interest in finance began at just 11 years old, when a holiday job with an advisor introduced him to the fast-paced financial services world. In his 20s, Mathew grew more aware of the lack of transparency in fees and services, which inspired his commitment to making financial advice clear and accessible. He reflects these values at Optimize.
Education is one of his top priorities. He believes clients shouldn’t need a finance degree to understand their money, and takes pride in breaking down complex concepts into straightforward insights.
Outside of work, Mathew enjoys spending time with his wife, young daughter, and dog, often exploring trails by the beach.
- Email: mathew.cain@optimizewealth.com
- Phone: (437) 253-7766
Team values
Client-First Approach
The Gray Team prioritizes exceptional, personalized service, treating every client as an individual with unique goals and circumstances. We focus on building trust and fostering meaningful relationships, meaning that each client feels supported, understood, and valued. Our client-first philosophy guides every recommendation and strategy, making sure that our solutions are aligned with your goals and designed to deliver long-term financial success and peace of mind.
Integrity as a Guiding Principle
Integrity is the foundation of everything The Gray Team does. We are committed to honesty, transparency, and ethical practices in every aspect of our work. Our team provides clear, unbiased advice and maintains open communication, always placing your best interests at the forefront. This dedication builds strong, trusted partnerships that inspire confidence and support your long-term financial goals.
Our dedication to excellence is
reflected in every aspect of our work
Clients can expect a proactive, high-touch experience designed to simplify and enhance their financial lives. At 4 Pillars Wealth, we believe in consistently going above and beyond to deliver exceptional service and build lasting relationships. This means not only addressing clients' current needs but also anticipating future challenges and opportunities, helping them feel confident and prepared for what lies ahead.
Empowering Clients Through Knowledge
The Gray Team firmly believes that informed clients make stronger decisions. That’s why we stay current with industry trends and emerging strategies, offering expert guidance that reflects today’s evolving financial landscape. Through education, we empower our clients with the knowledge they need to make well-informed choices, fostering confidence every step of the way.
Supporting our community
The Gray Team is committed to supporting equitable education for children in low-income communities. Through our involvement with First Book Canada, we help eliminate barriers to learning by providing essential resources and opportunities for students and educators. This reflects our dedication to building a brighter future, where every child has access to quality education and the support needed to succeed.
Supporting children’s health is another priority for our team. Through our contributions to SickKids, we help fund innovative pediatric research and world-class healthcare. Our support plays a role in improving health outcomes for young patients while offering hope and comfort for families, reinforcing our commitment to healthier, stronger communities.
The Gray Team values cultural understanding and reconciliation as part of our broader commitment to community impact. By supporting the Gord Downie & Chanie Wenjack Fund, we help foster meaningful dialogue and connection between Indigenous and non-Indigenous communities across Canada. This involvement reflects our belief in a more inclusive, unified, and compassionate future for all.