Systems & Technology Training Specialist

Job summary

Lead one-on-one and small group training sessions to drive the adoption of CRM and advisor portal tools. Guide financial advisors through system-driven workflows and provide live technical support.

Job details

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. Use of Artificial Intelligence in Recruitment As part of our recruitment and selection process, we may use technology-enabled tools, including artificial intelligence (AI), to assist with certain aspects of candidate screening, assessment, scheduling, and application review. All hiring decisions are ultimately made by qualified individuals and are based on job-related criteria, qualifications, and business requirements.

What you’ll do

Lead one-on-one and small group training sessions to drive the adoption of CRM and advisor portal tools. Guide financial advisors through system-driven workflows and provide live technical support.

Requirements

Requires a minimum of 2 years of professional experience in delivering one-on-one training or coaching. Candidates must possess strong communication skills and the ability to explain technical concepts to non-technical users.

Listed skills

• Problem solving · Preferred
• interpersonal skills · Preferred
• Coaching · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Systems Training
• Coaching
• CRM Proficiency
• Technical Communication
• Presentation Skills
• Interpersonal Skills
• Workflow Management
• Problem Solving
• Client Management
• Screen Sharing

Job areas

• Education
• Finance & Accounting
• Customer Service & Support
• Technology