Milestone Technologies, Inc.

Senior AI Engineer

Milestone Technologies, Inc.  •  Onsite  •  27 days ago
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Job Description

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.
Milestone Technologies, Inc.

About Milestone Technologies, Inc.

Milestone Technologies is a global IT Services and Digital Solutions company based in Silicon Valley that helps hundreds of leading corporations deliver technology around the globe.

We work with the world’s leading companies to deliver services and technologies at scale, accelerate digital operations, develop innovative applications, and drive efficiencies throughout their organization.

Milestone is focused on building an employee-first, performance-based culture, and for over 25 years, we have demonstrated a 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.

Follow us on:

Facebook: https://www.facebook.com/MilestoneTechnologiesInc

Twitter: https://twitter.com/MilestoneTech

Blog: https://milestone.tech/blog/

Industry
IT & Software
Company Size
1,001-5,000 employees
Headquarters
Fremont, California
Year Founded
1997
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