You will build on a modern learning stack anchored on Skilljar and Instruqt. You will make AI a core part of how customers are implemented, using agents to produce content, coach learners, and run learning operations.
RESPONSIBILITIES
Own the training journey for customer implementation training, focused on admins, IT, security, DevOps teams and non-developer teams adopting Docker Sandboxes and AI governance products.
Own the learning technology stack built on Skilljar and Instruqt, including catalog and learning-path structure and authoring workflows
Build hands-on: author the first implementation paths, labs, and assessments, and configure and administer Skilljar and Instruqt.
Design the training practice to be AI-native using built in features from Skiljar and Instruqt and support from Professional Services engineers: agents draft courses, lab guides, and assessments from product docs, release notes, and engineering changes, and flag stale content, with an SME review gate for technical accuracy before anything is published.
Establish repeatable curriculum standards: implementation path templates, hands-on lab patterns, assessment and badging criteria, content review and refresh cycles and web-based customer journeys.
Partner with technical subject-matter experts within Professional Services to build content, and support them on authoring in Instruqt.
Use AI agents, vendors, contractors, and SMEs as leverage to scale output ahead of headcount.
Define team model: roles, sequencing, and the business case for first hires.
Ensure learner data practices meet Docker’s privacy, security, and vendor review standards, including PII minimization and DPA requirements for training platforms and any AI models that process learner data.
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QUALIFICATIONS
REQUIRED
10+ years in technical training, customer education, or enablement leadership at a SaaS/infrastructure company, including 5+ years leading programs or teams, with a record of building a function from the ground up.
Comfortable as a hands-on builder and sole practitioner, with the ability to hire and lead a team as the function grows.
Demonstrated ability to influence senior stakeholders and technical contributors and drive alignment without formal authority.
Hands-on experience with an enterprise LMS (Skilljar preferred) and learner journey design.
Experience building and running customer implementation, onboarding, or education programs, including instructional design, hands-on labs, and certification or badging.
Experience with AI/ML and agentic AI concepts, and the ability to build training for AI workloads in enterprise environments.
Proven record of measuring training impact, using implementation completion, adoption, and business metrics, including retention, expansion, and revenue contribution, to show ROI to executives.
PREFERRED
Hands-on experience applying AI and LLM tools to content production, learner support, or learning operations, with clear human review and quality controls.
Experience building agent-based or MCP-integrated learning and documentation experiences, including AI lab coaching and automated assessment.
Experience managing vendors and platform engagements, including professional services partners and internal engineering dependencies.
BONUS
Strong technical credibility in containerization, container and software supply chain security, and enterprise IT and identity environments, with the ability to evaluate content quality alongside engineers.
Experience linking customer education to implementation completion, retention, and time-to-value metrics in a customer success or CRM platform.
Experience unifying documentation and learning platforms into a single SSO-authenticated learner experience.
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WHAT TO EXPECT
FIRST 30 DAYS
Onboard to Docker’s mission, values, and operating model.
Deeply familiarize yourself with our product portfolio, customers, and the current customer implementation journey, including provisioning, implementation engagements, and handoffs.
Build strong partnerships with Professional Services leaders, along with Skilljar, Instruqt, and vendor professional services contacts.
Plug into the team’s rhythm of business (standups, reviews, shadow customer implementation engagements).
FIRST 90 DAYS
You will be supported in the first 90 days by Professional Services SMEs, vendor professional services teams, and contractors.
Define the customer implementation training strategy, charter, and operating model, including audiences, intake and prioritization, and success metrics.
Launch a baseline analytics view of implementation milestone completion, badging, and adoption for executive reporting.
Ship the first priority implementation paths with hands-on labs, and establish a badging framework.
Pilot an AI-assisted content workflow with an SME review gate, and define the AI governance model for learner data and generated content.
ONE-YEAR OUTLOOK
A proven, data-backed Training practice with first hire(s) in place or approved and a defined team roadmap.
AI agents handle the majority of content drafting, refresh detection, and reporting, so a lean practice can scale ahead of headcount, with an AI lab coach and personalized implementation paths live for customers.
Measurable improvement in implementation completion, on-time provisioning, and time-to-value, with training demonstrably linked to adoption, retention, expansion, and revenue contribution.
New product capabilities launch with implementation training and labs ready on day one, and continuous improvement is institutionalized through learner analytics and customer feedback.
Visa sponsorship: Not available for this role.
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COMPENSATION & EQUITY
All full-time roles include equity. Final compensation is determined on factors including but not limited to experience, skills, qualifications, and location.
Canada: CA$179,149 - CA$255,927 base
United States: $131,495 - $187,850 base
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POSTING INFORMATION
Open vacancy: This posting is for an existing open role.
AI in hiring: Docker may use AI-assisted tools during our recruiting process.
Interview recordings: Candidates will be invited to opt in to interview recordings to support interviewer calibration and consistent evaluations. Recordings are optional and require explicit consent.
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PERKS & BENEFITS
Remote-first by design – Work from your home, with offices in Seattle and Paris for connection and collaboration.
Flexibility that fits your life – We trust you to manage your schedule while delivering great work.
Time to recharge – Generous PTO, designated quarterly Whaleness Days, and a designated end-of-year Whaleness break.
Home office support – Set up your workspace for comfort and success.
Technology stipend – Equivalent to US$100 net per month to help support your work.
Learning & development – Annual stipend for conferences, courses, certifications, and continued learning.
Parental leave – 16 weeks of paid parental leave after six months of employment.
Equity for all full-time employees – Share in Docker's long-term success as we continue to grow.
Comprehensive benefits – Medical, retirement, and paid holidays vary by country.
Docker swag – Because representing the whale never gets old.
Docker is proud to be an equal opportunity employer. We are committed to building a team that reflects a broad range of backgrounds, experiences, and perspectives. We believe diverse teams build better products, make better decisions, and better serve our global community.
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