Senior Manager, Training

Accountabilities:: Own and develop the end-to-end customer implementation training strategy, focusing on administrators, IT and security professionals, DevOps teams, and non-developer audiences adopting AI governance and sandbox technologies. Build and manage the learning technology ecosystem, including enterprise learning platforms such as Skilljar and Instruqt, overseeing course catalogs, learning paths, platform administration, and content authoring workflows. Personally design and deliver the initial implementation learning journeys, including training modules, hands-on labs, assessments, and certification or badging programs. Establish an AI-native training model by leveraging AI tools and agents to generate course materials, lab guides, assessments, learner support resources, and content updates based on product documentation and engineering changes. Implement quality assurance processes, ensuring all AI-generated training materials undergo appropriate subject-matter expert reviews before publication. Develop standardized curriculum frameworks, implementation templates, practical lab methodologies, assessment criteria, content refresh cycles, and digital customer learning experiences. Collaborate with Professional Services engineers and technical subject-matter experts to develop accurate, relevant, and engaging training content. Leverage AI agents, external vendors, contractors, and internal experts to increase training output and scale operations efficiently ahead of team expansion. Establish performance measurement frameworks and dashboards to track learner progress, implementation milestones, certification completion, product adoption, and customer outcomes. Demonstrate the business impact and return on investment of training initiatives by connecting learning performance to implementation completion, time-to-value, customer retention, expansion, and revenue contribution. Define the future structure of the Training function, including team responsibilities, hiring priorities, resource requirements, and a business case for additional hires. Ensure training platforms and AI-powered learning solutions comply with privacy, security, and vendor governance requirements, including personal information minimization and data processing agreements. Build strong relationships with senior stakeholders across Professional Services, Technical Account Management, and customer onboarding teams to align training initiatives with broader business objectives. Continuously improve learning experiences through customer feedback, learner analytics, and evolving product capabilities. Requirements: At least 10 years of experience in technical training, customer education, or enablement leadership within a SaaS, infrastructure, or technology company. At least 5 years of experience leading training programs or teams, with a proven track record of building and scaling a training or customer education function from the ground up. A hands-on leadership approach, with the ability to operate independently as an individual contributor while developing the strategy and capabilities required to build a team. Demonstrated experience designing and managing enterprise learning journeys, customer onboarding programs, and implementation training initiatives. Practical experience with enterprise Learning Management Systems (LMS), preferably Skilljar, including platform configuration, administration, and learning path development. Strong instructional design capabilities, including experience developing technical courses, hands-on labs, assessments, certifications, and digital learning experiences. Experience with artificial intelligence, machine learning, and agentic AI concepts, with the ability to develop training programs for enterprise AI workloads. Strong stakeholder management and communication skills, with the ability to influence senior leaders, technical experts, and cross-functional contributors without relying on formal authority. Proven ability to measure training effectiveness using implementation, adoption, and business performance metrics, and communicate return on investment to executive stakeholders. Excellent strategic planning, organizational, and project management skills, combined with a strong focus on execution and measurable results. Additional qualifications considered an asset: Hands-on experience using AI and large language models (LLMs) for content development, learner assistance, and learning operations, supported by appropriate human oversight and quality controls. Experience developing agent-based or Model Context Protocol (MCP)-integrated learning and documentation experiences, including AI-powered lab coaching and automated assessments. Experience managing external vendors, professional services partners, and internal engineering dependencies. Strong technical knowledge of containerization, container and software supply chain security, enterprise IT, and identity management environments. Experience connecting customer education initiatives to implementation completion, customer retention, and time-to-value metrics through CRM or customer success platforms. Familiarity with integrating documentation and learning platforms into a unified, single sign-on (SSO) authenticated learner experience. Experience developing scalable learning operations using automation, analytics, and AI-powered tools. Benefits: Competitive annual base salary in Canada: CAD 179,149–255,927, depending on experience, skills, qualifications, and location. Equity participation for all full-time employees, providing an opportunity to share in the organization's long-term growth. Fully remote-first working environment, with the flexibility to work from home. Flexible working schedules and autonomy in managing your time and responsibilities. Generous paid time off (PTO). Dedicated quarterly wellness days and an additional end-of-year wellness break. Home office support to help create a comfortable and productive workspace. Monthly technology stipend equivalent to US$100 net to support work-related technology needs. Annual professional development allowance for conferences, courses, certifications, and continued learning. 16 weeks of paid parental leave after six months of employment. Comprehensive medical and healthcare benefits, retirement programs, and paid holidays, depending on the country of employment. Opportunities to work with innovative technologies and contribute to the development of AI-powered customer education solutions. Access to a collaborative, globally distributed team and opportunities for professional growth. Company merchandise and additional employee perks. Additional information: This is an existing, open full-time position. The role is available remotely in Canada and the United States. Visa sponsorship is not available for this position. Interview recordings may be offered to support consistent evaluation and interviewer calibration; participation is optional and requires candidate consent.