Senior Manager, Training

New

DockerDeveloper tooling, SaaS infrastructure

Location: Canada; Secondary Locations: United States; Workplace: RemoteFull-TimeManager

SalaryCanada: CA$179,149 - CA$255,927 base; United States: $131,495 - $187,850 base

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Job Details

Experience: 10+ years in technical training, customer education, or enablement leadership at a SaaS/infrastructure company, including 5+ years leading programs or teams

Have 10+ years of experience in technical training, customer education, or enablement leadership at a SaaS or infrastructure company.
Have 5+ years leading programs or teams and a record of building a function from the ground up.
Be comfortable as a hands-on builder and sole practitioner, with the ability to hire and lead a team as the function grows.
Demonstrate experience influencing senior stakeholders and technical contributors and driving alignment without formal authority.
Bring hands-on experience with an enterprise LMS; Skilljar is preferred.
Have experience designing learner journeys and building customer implementation, onboarding, or education programs.
Have experience with instructional design, hands-on labs, and certification or badging.
Understand AI/ML and agentic AI concepts and be able to build training for AI workloads in enterprise environments.
Show a record of measuring training impact using implementation completion, adoption, and business metrics to demonstrate ROI to executives.
Preferred: apply AI and LLM tools to content production, learner support, or learning operations with human review and quality controls.
Preferred: build agent-based or MCP-integrated learning and documentation experiences, including AI lab coaching or automated assessment.
Preferred: manage vendors and platform engagements, including professional services partners and internal engineering dependencies.

Own customer implementation training journeys for admins, IT, security, DevOps, and non-developer teams adopting Docker products.
Own the learning technology stack built on Skilljar and Instruqt, including the catalog, learning paths, and authoring workflows.
Build initial implementation paths, hands-on labs, and assessments, and configure and administer Skilljar and Instruqt.
Design AI-assisted content workflows that draft courses, lab guides, and assessments and flag stale content, with SME review for technical accuracy.
Establish curriculum standards, including implementation path templates, lab patterns, assessment and badging criteria, and content review cycles.
Partner with Professional Services subject-matter experts to build content and support their Instruqt authoring.
Use AI agents, vendors, contractors, and SMEs to scale training output ahead of headcount.
Define the training team model, hiring sequence, and business case for initial hires.
Ensure learner data practices meet privacy, security, and vendor review standards, including PII minimization and DPA requirements.
Measure training impact against implementation, adoption, retention, expansion, and revenue metrics.

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