Senior Manager, Training

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Take ownership of the training process for customer implementation education aimed at admins, IT, security, DevOps, and non-developer teams utilizing Docker Sandboxes and AI governance solutions.

• Manage the Skilljar and Instruqt learning technology ecosystem, encompassing the catalog, learning-path framework, and authoring processes.

• Create the initial implementation pathways, labs, and assessments.

• Set up and oversee Skilljar and Instruqt.

• Develop an AI-driven training approach using agents to generate courses, lab manuals, and assessments while identifying outdated content, with technical review from subject-matter experts prior to publication.

• Establish standards for curriculum, templates for implementation paths, lab formats, assessment and badging criteria, content refresh schedules, and web-based customer experiences.

• Collaborate with Professional Services subject-matter experts to create content and facilitate Instruqt authoring.

• Utilize AI agents, vendors, contractors, and subject-matter experts to enhance output in advance of team expansion.

• Define team roles, sequencing, and the justification for initial hires.

• Ensure learner data practices comply with Docker's privacy, security, vendor review, PII minimization, and DPA standards.

• Establish the strategy for customer implementation training, including charter, operating model, target audiences, intake, prioritization, and success metrics.

• Implement analytics to track completion of implementation milestones, badging, and adoption reporting.

• Deliver priority implementation paths with practical labs and create a badging framework.

• Test an AI-assisted content workflow and establish AI governance for learner data and generated materials.

• Develop a data-informed training practice to enhance implementation completion, provisioning, time-to-value, adoption, retention, expansion, and revenue contributions.

⛳️ Requirements

• Over 10 years of experience in technical training, customer education, or enablement leadership within a SaaS/infrastructure organization.

• More than 5 years of experience leading programs or teams.

• Proven track record of establishing a function from the ground up.

• Comfortable as a hands-on builder and independent practitioner, with the capability to hire and lead a team as the function expands.

• Ability to sway senior stakeholders and technical contributors and foster alignment without formal authority.

• Practical experience with an enterprise LMS; Skilljar is preferred.

• Proficiency in learner journey design.

• Experience in developing and managing customer implementation, onboarding, or educational programs.

• Background in instructional design, practical labs, and certification or badging.

• Familiarity with AI/ML and agentic AI concepts.

• Capability to create training for AI workloads in enterprise settings.

• Demonstrated ability to assess training impact using metrics related to implementation completion, adoption, retention, expansion, and revenue contributions.

• Preferred: experience utilizing AI and LLM tools for content creation, learner support, or learning operations, with human review and quality assurance.

• Preferred: experience in creating agent-based or MCP-integrated learning and documentation experiences, including AI lab coaching and automated assessment.

• Preferred: experience in managing vendor relationships and platform engagements.

• Bonus: technical expertise in containerization, container and software supply chain security, and enterprise IT and identity environments.

• Bonus: experience in correlating customer education with implementation completion, retention, and time-to-value metrics in a customer success or CRM system.

• Bonus: experience in integrating documentation and learning platforms into a unified SSO-authenticated learner experience.

• Must have legal authorization to work in the country where applying.

• Visa sponsorship is not available for this position.

🏝️ Benefits

• Designed to be remote-first – Work from home, with offices in Seattle and Paris for connection and collaboration.

• Flexibility to accommodate your life – Manage your schedule while delivering exceptional work.

• Generous paid time off (PTO).

• Designated quarterly Whaleness Days.

• Scheduled end-of-year Whaleness break.

• Support for home office setup.

• Technology stipend of US$100 net per month.

• Annual stipend for conferences, courses, certifications, and ongoing learning.

• 16 weeks of paid parental leave after six months of employment.

• Equity options for all full-time employees.

• Medical, retirement, and paid holiday benefits vary by country.

• Docker merchandise.