Your partner in personalized, full-service wealth management

For families and businesses across Western Canada, managing wealth today means navigating complex markets, major life transitions, and long-term financial goals. Sheldon Gray is a seasoned financial expert with over three decades of experience in investment management, insurance, banking, and agriculture. Known for his client-first approach and deep expertise, he has built a strong track record in portfolio management, business development, and strategic advisory roles.

Based in Regina, SK, Sheldon currently advises clients with Optimize Wealth Management. He has also held leadership roles with Wellington-Altus Private Wealth, Scotia Wealth Management, CIBC, and Farm Credit Canada. At Scotia, he managed growth of a $300 million book of business, introduced portfolio management services to Saskatchewan, and mentored advisory teams to consistently deliver strong results.

His expertise includes investment strategy, financial and retirement planning, credit structuring, and risk management. He has guided clients through complex transitions, developed equity models, and guided clients to a successful retirement.

Beyond the office, Sheldon remains active in his community. He serves as President of a condominium association and contributes to organizations including Pickleball Regina and the Kiwanis Club of Regina-Wascana. Sheldon is an avid hockey, baseball, and pickleball player.

Sheldon holds the CIM, CFP, and FEA designations, along with a B.Sc. in Agriculture from the University of Manitoba. A lifelong learner, he continues to pursue professional development to ensure clients benefit from the most current knowledge and strategies.

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.