Software Trainer Jobs in Ontario (NOW HIRING)

What You'll Do

Reporting to the Professional Services Manager, you will:

• Own and deliver live virtual and on-site software training for SpaSoft customers across multiple time zones
• Lead application consultation and system configuration, guiding customers through best practices aligned with their operational needs
• Provide hands-on go-live support, ensuring a smooth transition and confident system adoption (including extended hours when required)
• Review customer documentation and perform pre-implementation setup and data validation
• Design, document, and educate customers on custom workflows, operational procedures, and system optimization
• Create and maintain enablement content including LMS courses, knowledge base articles, help documentation, and internal playbooks
• Continuously evaluate and improve training materials based on customer feedback and product evolution
• Stay current on new features, modules, integrations, and platform updates in a SaaS environment
• Collaborate cross-functionally with Support, Product, and Professional Services teams to improve the customer journey
• Participate in product testing, feedback loops, and documentation to influence product quality and usability
• Step in to support customers by logging and resolving support cases when needed
• Manage multiple projects simultaneously, owning timelines, priorities, and stakeholder communication
• Assist Senior Trainers or Project Managers on larger or more complex implementations when applicable
• Deliver internal training sessions to upskill teams and promote product knowledge
• Actively participate in the EDGE customer-first process, ensuring exceptional customer satisfaction
• Attend in-person meetings or on-site engagements as required
• Take on additional responsibilities as the business grows - we value initiative

What We're Looking For

• Associate's or Bachelor's degree preferred
• 2+ years of experience in software training, enablement, implementation, or customer education
• Proven ability to self-manage projects, prioritize effectively, and deliver results with minimal supervision
• Strong problem-solving mindset with comfort navigating ambiguity and evolving requirements
• Ability to learn quickly, adapt fast, and thrive in a high-growth SaaS environment
• Experience working directly with customers in hospitality, hotel, spa, or wellness operations is a strong plus
• Background in customer support, technical consulting, or onboarding is an asset
• Confident presenter with experience in public speaking, facilitation, or instructional design
• Experience creating digital learning content, including videos, webinars, and online courses
• Strong written and verbal communication skills - clear, concise, and customer-focused
• Comfortable using modern workplace tools (Microsoft Office, Outlook, Teams, Excel, PowerPoint)
• Willingness and ability to travel internationally (valid passport required)
• While remote, there are possibilities to be asked to be at the office for meetings and other gatherings

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas' vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of "Software for Life." We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We're a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.