Software Training Specialist (AI-Enabled Learning & Content)

Software Training Specialist

Mississauga , Ontario – Hybrid (4 days/week in office)

* Moving to Etobicoke 2026*

Mattamy Asset Management

IT Enterprise Services

Full-Time

Vice President , IT Portfolio & Planning

At Mattamy Asset Management ( MAM ) , everyone has an important role to play in our shared success. Developing thoughtfully planned communities is complex work and our diverse teams come together to deliver on that mission in every aspect. We are thoughtful planners, precise project managers and practiced subject matter experts. And in each area of our evolving business, we are trusted to drive results. Here, your opinion will be invited, and your contributions will count. You’ll be surrounded by caring people who encourage you to be exactly who you are. You’ll grow in your area of expertise, learning alongside committed colleagues. With a relentless focus on industry leadership and a deep commitment to sustainability, we’ve got big plans for the future – and for you.

Learn more about what makes working at Mattamy special and our award-winning culture.

What we offer

We are seeking a Software Training Specialist who leverages modern AI tools to create practical, high impact enablement content that helps employees succeed in their day-to-day work. Rather than focus on traditional training alone, this role is centered on role - based, task-oriented support ( learning paths, job aids, quick reference guides, and AI powered knowledge ), designed so employees can get answers and support at the moment of need. Acting as both a content creator and enablement strategist, you’ll partner closely with IT, product teams, and business stakeholders to translate workflows, system changes, and business needs into scalable learning experiences that drive measurable adoption and productivity.

What you’ll do

• Design and produce AI generated and AI augmented enablement content, including role - based learning paths, task level job aids, SOPs, walkthroughs, simulations, and quick reference guides.
• Use AI tools (e.g., Microsoft Copilot and similar platforms) to accelerate content creation, automate documentation, summarize workflows, and personalize learning assets.
• Rapidly translate business inputs (process documentation, system changes, support tickets, feedback, and workflows) into usable, high impact learning content.
• Create role-based enablement materials aligned to real day-to-day workflows, with a focus on “how do I do my job today?” rather than system features alone.
• Partner with business and IT stakeholders to define critical tasks by role and map those tasks to the right learning and performance support assets.
• Design learning experiences that support onboarding, role transitions, and continuous skill development.
• Work with a Learning Management System (LMS), including course setup, content uploads, and learning paths (experience with platforms such as Saba, Cornerstone, Docebo, or similar).
• Ensure strong content governance, including version control, lifecycle management, archiving outdated materials, and consistency across all enablement assets.
• Promote adoption of self-service learning resources and continuously refine how content is discovered and consumed.
• Design knowledge checks, validations, and assessments to ensure understanding and retention where appropriate.
• Leverage AI driven insights, usage data, and learner feedback to identify adoption gaps, workflow friction, and opportunities for improvement.
• Measure training and enablement effectiveness using adoption, behavior change, productivity, and user experience indicators ( not just course completion ) .
• Provide ongoing recommendations to improve enablement strategies, learning design standards, and content effectiveness.
• Deliver virtual or onsite instructor led training sessions when needed, using tools such as Microsoft Teams or Zoom
• Coordinate training logistics, scheduling, and communication for sessions and learning launches.
• Establish and maintain strong relationships with stakeholders through clear communication, collaboration, and responsiveness.
• Proactively identify risks, issues, and dependencies related to enablement initiatives and communicate effectively with project teams

What y ou b ring

• 3+ years of experience creating learning and enablement content, including role-based materials that support day-to-day business operations
• Associate’s degree or equivalent experience in training, learning design, communications, or a related field.
• Hands ‑ on experience using   AI productivity tools  (e.g., generative AI, Microsoft Copilot, or similar) to create, refine, and scale learning content.
• Strong ability to translate complex workflows, systems, and processes into clear, actionable learning assets.
• Experience managing and structuring content within an LMS or knowledge platform.
• Understanding of adult learning principles and modern enablement practices (micro ‑ learning, performance support, contextual learning).
• Excellent organizational and project management skills, with the ability to manage multiple initiatives and prioritize independently.
• Strong communication and relationship ‑ building skills; comfortable working with stakeholders of varying technical backgrounds.
• Willingness to travel approximately 30–45% across Canada and the United States.

Bonus points

• Homebuilding or construction industry experience

Compensation

The expected base salary range for this position is $70,000 - $110,000 . Actual pay may vary depending on your job-related knowledge, competencies , and skills. We recognize that exceptional situations may fall outside this range, and we encourage all interested candidates to apply.

You are also eligible to participate in Mattamy’s annual bonus program which gives you the opportunity to increase your total compensation if business and individual goals are achieved.

We encourage applicants who meet most of the role requirements to hit that submit button and apply! It’s okay if you don’t have 100% of the requirements. If you’re the right candidate, we’ll help you learn and grow.

Who we are

Mattamy Asset Management (MAM) is the parent company of Mattamy Homes Canada and Mattamy Homes U.S., which together make up the largest family-held homebuilding platform in North America.

Be yourself. We want it that way.

At Mattamy, we're passionate a ​ b ​​ out creating and promoting a diverse and inclusive environment where everyone ​ can do their best work. Diversity and inclusion are important to the work we do to support our homebuyers, colleagues, and communities. From how we build our teams to cultivating our leaders, we're on a journey toward a welcoming, barrier-free culture for everyone. ​​​​

Mattamy Asset Management is committed to providing accommodation for people with disabilities. If you require accommodation through any aspects of the selection process, please notify us on your application and we will work with you to meet your needs.

Mattamy companies may use artificial intelligence (AI) tools to support our hiring process, including to help screen or assess candidates along the way. These tools work behind the scenes, while people remain at the heart of every hiring decision.

Qualified applicants for this existing vacancy will be contacted directly by the Talent Acquisition team.