Meet Our Team


LEE SMALLWOOD LLQP, CFP

President & CEO

Lee Smallwood the Principal and Founder of First Five Insurance & Investments is a graduate of the Accounting and Finance program at Seneca College, a C.G.A associates and holds a C.F.P certification in financial planning. Lee has held several Senior Executive positions in accounting as Controller, Corporate Controller and VP of Finance. Over the last six years Lee Smallwood was a Regional Portfolio Manager for the public traded company; Northern Property Real Estate Investment Trust – the second largest residential real estate company in Canada. In his role at Northern Property Real Estate Investment Trust; Lee oversees a staff of thirty and a portfolio valued at more than two hundred fifty millions dollars. In addition, he also oversees the rebirth and turnaround of the Inuvik Chamber of Commerce. For more about Lee Smallwood please check: firstfivebookkeeping.com, Inuvikhamber.com and LinkedIn bio.


ROY SMALLWOOD LLQP, RIBO

VP Insurance Sales

Roy Smallwood obtained his Life Insurance License and began his career as a part time Insurance Agent in 2011. In 2014 Roy left his full time chef position to joined Alliance Financial Group as a full time Licensed Insurance Advisor. Roy has a passion for helping his clients protecting their families using various Insurance and Investment products. His clients consider him to be an Insurance Professional with a personal touch. His philosophy remains the same, “use insurance to help mitigate and manage risk and protect the things you value most.” As such, he takes pride in educating his clients while maintaining a lasting professional relationship. Roy has a drive to learn new things and constantly challenges himself. In 2015 he obtained his RIBO (Registered Insurance Brokers of Ontario) Insurance license through the Insurance Brokers Association of Ontario. A RIBO Insurance License allows him to serve his clients’ commercial properties and auto insurance needs.


We are always looking for qualified candidates!

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