Job Description

ROLE PURPOSE

Own training and enablement across the entire programme, and act as the offshore agile coaching anchor. The role designs and delivers persona-based learning for a heterogeneous audience — from engineering teams to corporate functions — with training intensity that scales by wave complexity, and supports the broader OCM effort in partnership with the onshore OCM Lead and Agile Coach.

KEY RESPONSIBILITIES

• Design the end-to-end training strategy and curriculum for Jira Cloud and Confluence Cloud, segmented by persona: technical delivery teams (developers, QA, RTEs, Scrum Masters, product owners, architects) and non-technical functional teams (corporate functions, PMO, commercial, operations).
• Scale training intensity to the wave model: self-serve and standard assets for Wave 1 (lower complexity), wave-specific guided training for Wave 2, and role-based, customized, hands-on preparation for Wave 3 (complex/integrated projects).
• Build and maintain the enablement library: quick-start guides, job aids, how-to videos, onboarding modules, FAQs, and greenfield onboarding paths for users new to Jira/Confluence.
• Launch and nurture Communities of Practice and champion networks; run Lunch & Learn sessions, workshops, and office hours across US, EU, and APAC time zones on a predictable calendar.
• As offshore agile coach, reinforce SAFe-aligned ways of working in the new environment — backlog hygiene, boards, PI planning artifacts, ART dashboards — in coordination with the onshore Agile Coach.
• Embed AI-capability content (developed with the Senior AI Engineer) into curricula so AI adoption is trained as part of normal ways of working, not as a separate initiative.
• Track training completion, satisfaction, and post-training usage; feed insights to the OCM Lead and programme reporting.

REQUIRED QUALIFICATIONS & EXPERIENCE

• 8+ years across Atlassian administration/SME work and enterprise training or enablement leadership; deep hands-on Jira and Confluence knowledge (cloud experience strongly preferred).
• Proven design and delivery of persona-based training programmes for global, multi-time-zone audiences at enterprise scale.
• Agile coaching credibility: SAFe (SPC/RTE), Scrum Alliance, or equivalent certification, with practical coaching experience.
• Strong content-development craft across written, video, and live formats; comfort with LMS and content tooling.
• Facilitation excellence in both technical and non-technical rooms.

PREFERRED

• Prior enablement work on a Data Center-to-Cloud (or equivalent platform) migration.
• Experience partnering with formal OCM functions and communications teams.
• Familiarity with adoption analytics and sentiment measurement.

ENGAGEMENT MODEL

This is a time-and-materials staff augmentation position. The individual operates as a member of Client's programme organization; the direction, prioritization, and acceptance of work rest with Client. Milestone provides qualified professionals and delivery oversight support; migration execution, platform ownership, tooling decisions, and programme outcomes remain with Client.