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Company Overview
Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.
Our seasoned professionals deliver services based on Milestone’s best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.
Job Overview
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.
Compensation
Estimated Pay Range:
Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.
Our Commitment to Diversity & Inclusion
At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for our employees but is also critical to our continued success.
Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.
We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.
