Training & Development Specialist

Training & Development Specialist

This role will support a major AI-enabled business transformation as operations transition from a legacy environment to Salesforce. You will design and deliver learning experiences that help employees adopt new systems, processes, and ways of working with confidence. The position combines learning design, training delivery, business readiness, and stakeholder engagement across a large-scale transformation. You will create role-based curricula, training materials, job aids, and knowledge resources tailored to diverse audiences. The role requires close collaboration with business leaders, subject matter experts, technology teams, project managers, and change stakeholders. You will also monitor readiness and adoption, identify learning gaps, and develop reinforcement strategies that support sustainable behavioral change. This is an opportunity to make a measurable impact on employee experience while helping minimize disruption throughout a complex technology transformation.

Accountabilities:

• Develop and execute a comprehensive training strategy aligned with the transition to Salesforce, project milestones, and deployment schedules.
• Conduct learning needs assessments and training impact analyses to identify capability gaps and define appropriate learning solutions.
• Design role-based curricula, learning journeys, and adoption plans that prepare employees for new processes, systems, and responsibilities.
• Create instructor-led, virtual, and self-paced training materials, job aids, process documentation, and other learning resources for diverse audiences.
• Translate future-state business processes into clear, practical, and engaging training content while keeping materials aligned with evolving system and business requirements.
• Maintain knowledge repositories and ongoing support resources to ensure employees can access relevant information throughout the transformation.
• Deliver engaging training sessions for employees, leaders, and support teams, adapting facilitation approaches to learner feedback and operational needs.
• Facilitate train-the-trainer sessions and knowledge transfer workshops while providing coaching and support during transition periods.
• Partner with change management and business readiness teams to assess organizational readiness and identify learning or adoption risks.
• Support user acceptance testing, pilots, deployments, go-live activities, and post-implementation stabilization by addressing learning gaps and readiness needs.
• Monitor training effectiveness and user adoption metrics and develop reinforcement strategies to sustain learning and long-term behavioral change.
• Collaborate with business leaders, subject matter experts, product teams, project managers, and transformation leaders throughout the project lifecycle.
• Provide regular updates on training readiness, risks, and mitigation strategies and participate in planning sessions, sprint reviews, design walkthroughs, and release readiness activities.

Requirements:

• Demonstrated experience designing and delivering training programs within large-scale business or technology transformation initiatives.
• Experience supporting system implementations, process transformations, digital modernization programs, or comparable organizational change initiatives.
• Strong facilitation, presentation, adult learning, and instructional design capabilities.
• Proven experience developing training content, learning assets, job aids, and documentation for diverse audiences.
• Strong ability to engage business stakeholders, understand organizational needs, and influence adoption outcomes.
• Exceptional written communication and documentation skills, with the ability to translate complex processes into clear learning materials.
• Experience supporting Salesforce implementations or CRM transformations is highly desirable.
• Experience in insurance, claims, financial services, or other highly regulated environments is an advantage.
• Understanding of change management and business readiness methodologies is preferred.
• Knowledge of Insurance & Investment Claims processes is considered a strong asset.
• Experience working within Agile project environments is desirable.
• Familiarity with learning technologies, LMS platforms, and digital adoption tools is a plus.
• Bilingual proficiency in English and French is an asset, while candidates based in Québec will require proficiency in both languages to support clients across multiple provinces.

Benefits:

• Salary range of $59,100 CAD to $98,500 CAD for the referenced Ontario location, with actual compensation varying based on factors such as location, skills, qualifications, experience, and education.
• Opportunity to participate in incentive programs with compensation tied to business and individual performance.
• Flexible work environment with a strong focus on employee wellbeing and inclusion.
• Customizable health and dental benefits for eligible employees.
• Mental health, vision, short- and long-term disability, life, and AD&D insurance coverage.
• Adoption, surrogacy, wellness, and employee/family assistance programs.
• Retirement savings options, including pension and employer-matched global share ownership opportunities for eligible employees.
• Financial education and counseling resources.
• Paid time off including holidays, vacation, personal, and sick days, along with statutory leaves of absence.
• Opportunities to learn, develop new skills, and shape long-term career growth within a global environment.
• Exposure to AI-enabled transformation, Salesforce, modern learning practices, and large-scale organizational change initiatives.