Senior AI Engineer

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

Enable Client to activate the AI capability that ships natively with Atlassian Cloud - and to use AI to accelerate the migration itself. The role works alongside Client's migration engineers and the Jira Cloud Architect: applying AI-assisted techniques to pre-migration cleanup and analysis, and building the prompt libraries, agent configurations, and adoption assets that turn platform-native AI into everyday productivity after each wave lands.

KEY RESPONSIBILITIES

• Configure, evaluate, and operationalize platform-native AI capabilities in Atlassian Cloud (Atlassian Intelligence, Rovo agents and search, AI-assisted automation) against Client-relevant use cases - prioritizing capability the platform licence already includes before any external tooling is considered.
• Support Client's migration engineering team with AI-assisted analysis at scale: classification and rationalization of workflows, custom fields, schemes, and Confluence content; duplicate and dormancy detection; anomaly surfacing in migration verification outputs.
• Build and maintain prompt libraries, agent playbooks, and use-case catalogues by persona (engineering, agile execution, business/functional teams), in partnership with the Training Lead and OCM Lead.
• Develop lightweight automation and scripts (e.g., Python against Atlassian REST APIs) that support migration-adjacent analysis, reporting, and adoption measurement.
• Define and track AI adoption measures across three axes - adoption (reach and correct usage), guardrails (responsible-use compliance), and business impact (time saved, cycle-time reduction) - and feed results into programme reporting.
• Contribute AI-enablement content to training assets, Communities of Practice, and champion networks; run targeted enablement sessions for high-leverage personas.
• Document configurations, evaluations, and recommendations so that capability transfers cleanly to Client teams at stabilization.

REQUIRED QUALIFICATIONS & EXPERIENCE

• 6+ years in software/data engineering with 2+ years hands-on in applied AI/LLM work: prompt engineering, agent configuration, retrieval patterns, and evaluation of AI outputs.
• Working proficiency with Python and REST APIs; ability to script analysis against large administrative datasets (workflows, fields, users, content).
• Practical familiarity with the Atlassian platform (Jira, Confluence) and its automation framework; ability to come up to speed quickly on Atlassian Intelligence and Rovo capabilities.
• A use-case-first working style: starts from the work and the measurable benefit, not from the tool.
• Clear documentation and enablement skills; comfortable presenting to non-technical audiences.

PREFERRED

• Experience with Atlassian Forge or Connect app ecosystems; exposure to Data Center-to-Cloud migration tooling.
• Experience defining responsible-AI guardrails in an enterprise (data handling, access boundaries, human-in-the-loop review).
• Exposure to regulated-industry constraints on AI usage.

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.