Systems & Technology Training Specialist Jobs in Toronto, Ontario, Canada
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Toronto, Ontario, Canada
Systems & Technology Training Specialist
About the role
About Optimize Financial Group
Optimize Financial Group is a premier financial services firm based in Toronto, ON, dedicated to helping clients achieve their long-term financial goals. We provide personalized financial solutions spanning portfolio management, tax planning, debt management, retirement planning, and estate strategies. Our holistic approach aligns financial objectives with life ambitions, ensuring every client receives a thoughtful and tailored path to success.
The opportunity
We are seeking a Systems & Technology Training Specialist to join our team at our Toronto office. In this role, you will lead one-on-one and small group training sessions with financial advisors, focusing on driving adoption and effective use of our core systems and technology platforms. You will deliver structured training on our CRM, advisor portal, and related tools, ensuring advisors are confident, efficient, and aligned with best practices. This is a full-time, on-site role, Monday to Friday, 8:30 a.m. to 5:30 p.m.
Key responsibilities
Lead one-on-one and small group meetings with advisors using a structured script and meeting agenda. Deliver live systems training and screen-sharing support on Optimize’s CRM, advisor portal, and related tools. Guide advisors through system-driven workflows, including client management, task tracking, and activity management. Respond to common questions, manage objections, and keep conversations on track while maintaining a professional and constructive tone. Reinforce clear next steps and follow-up actions after each meeting. Collaborate with internal teams to help ensure a consistent and high-quality advisor experience.
Qualifications
Minimum of 2 years of experience delivering one-on-one training or coaching sessions in a professional setting. Strong communication, presentation, and interpersonal skills with the ability to follow a script and lead structured conversations confidently. Strong ability to explain technical concepts clearly to non-technical users in a structured training environment. Strong organizational skills and the ability to follow a structured process while adapting in real time. Demonstrated proficiency in delivering live training, including screen sharing and guided walkthroughs. Professional, confident communicator with strong problem-solving skills and attention to detail. Experience with CRM platforms, advisor tools, or financial services technology is considered an asset.
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About Optimize Financial Group
At Optimize, we believe in creating wealth with intention. We offer a full suite of family office services, including financial planning, wills and estate planning, tax strategies, mortgages, loans, and insurance solutions, all designed to support every part of your financial life.
What sets our investment approach apart is its institutional strength. We focus on solid public companies with strong fundamentals, apply dynamic asset allocation that adapts to market shifts, and incorporate pension-style strategies that protect against downside risk while building lasting wealth.
Our holistic approach balances both protection and growth to give you the clarity and confidence to shape your financial future.