Senior Manager, Training

Jobgether; Canada; Remote; CAD 179,000 - 256,000; Full time

Benefits offered by this job

Fully remote-first environment

Monthly tech stipend US$100 net

Annual professional development budget

Generous PTO

Job summary

Jobgether is seeking a Senior Manager, Training to build and lead a customer education function from the ground up. You will design scalable learning journeys covering implementation, IT, security, DevOps, and AI governance for enterprise customers.

This remote-first role offers the opportunity to recruit a team as the function scales across a globally distributed tech environment. You will start hands-on, establishing learning tech infrastructure, practical training programs, and AI-powered

Qualifications

• 10+ years in technical training or enablement leadership.
• 5+ years leading training programs or teams.
• Hands-on leader who can work as IC while building a team.
• Experience designing enterprise learning journeys and onboarding programs.
• Experience with enterprise LMS, preferably Skilljar.
• Strong instructional design for technical courses and hands-on labs.
• Experience with AI/ML and agentic AI concepts.
• Strong stakeholder management and communication skills.
• Proven ability to measure training impact and ROI.
• Excellent strategic planning and project management.

Responsibilities

• Own end-to-end customer training strategy for admins, IT/security, DevOps, and non-developer audiences.
• Design and manage the learning tech ecosystem (LMS, content, catalogs, paths).
• Design and deliver initial implementation learning journeys with labs and assessments.
• Establish AI-native training models with AI tools for content generation and updates.
• Ensure quality with SME reviews for AI-generated materials.
• Develop curriculum frameworks, templates, labs, assessments, and certifications.
• Collaborate with Professional Services and engineers on training content.
• Leverage external vendors and internal experts to scale output.
• Develop dashboards to measure learner progress and outcomes.
• Demonstrate ROI and business impact of training initiatives.

Skills

Leadership

Strategic planning

Stakeholder mgmt

Instructional design

LMS administration

AI/ML familiarity

Project management

Tools

Skilljar LMS

Instruqt

Job description

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Senior Manager, Training based in Canada.

As Senior Manager, Training, you will build and lead a customer education and training function from the ground up, helping enterprise customers accelerate onboarding, product adoption, and time-to-value. You will design scalable learning journeys for technical and non-technical audiences, covering implementation processes, enterprise IT, security, DevOps, and AI governance solutions. Starting as a hands-on individual contributor, you will establish the learning technology infrastructure, develop practical training programs, and introduce AI-powered workflows to scale content creation and learner support. Working closely with Professional Services, engineering experts, and senior stakeholders, you will ensure training initiatives deliver measurable business outcomes. As the function expands, you will have the opportunity to recruit and lead a dedicated team. This is a high-impact leadership opportunity within a remote-first, globally distributed technology environment.

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.