About The Position

The Executive Office of Economic Development is seeking a hands-on System Administrator Contractor to support the upgrade and migration of approximately six legacy SQL Server and Windows Server environments hosted on AWS EC2. This role is ideal for a system administrator who is technically capable, eager to learn, and comfortable taking ownership of work with guidance from senior staff. The contractor will work closely with the EOED CISO, development leads, and EOTSS partners to plan and execute migrations from SQL Server 2012 to SQL Server 2019/2022 and corresponding Windows Server upgrades.

Requirements

  • Hands-on experience administering Windows Server environments.
  • Practical experience with SQL Server backup and restore.
  • Prior experience performing server or SQL upgrades (even at small scale).
  • Familiarity with cloud-hosted servers (AWS EC2 experience preferred).
  • Strong organizational skills and attention to detail.
  • Ability to work independently while knowing when to ask questions.
  • Clear written and verbal communication skills.

Nice To Haves

  • Exposure to SQL Server 2019 or 2022.
  • Basic scripting experience (PowerShell preferred).
  • Familiarity with development/test/production environment coordination.
  • Experience working in regulated or public-sector environments.

Responsibilities

  • Perform SQL Server upgrades and migrations (standalone instances) from legacy versions to SQL Server 2019 or 2022.
  • Support Windows Server upgrades to supported versions (2019/2022).
  • Execute SQL backup, restore, validation, and cutover activities.
  • Assist in evaluating high availability and disaster recovery requirements (with guidance).
  • Perform post-migration testing and validation with development teams.
  • Conduct and document backup restoration testing.
  • Produce RTO/RPO documentation for migrated systems.
  • Work with the CISO and development leads to build and manage migration plans.
  • Track tasks, dependencies, risks, and timelines to ensure migrations complete on schedule.
  • Coordinate with EOTSS as needed for infrastructure, access, or change activities.
  • Participate in change planning and scheduled cutovers.
  • Create and maintain clear documentation, including: Migration steps and runbooks. Testing and validation results. Known issues and follow-up items.
  • Provide regular status updates and escalate risks or blockers early.
  • Maintain professional, collaborative relationships across technical and non-technical teams.

Benefits

  • When you embark on a career with the Commonwealth, you are offered an outstanding suite of employee benefits that add to the overall value of your compensation package.
  • Explore our Employee Benefits and Rewards!

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What This Job Offers

Career Level

Entry Level

Education Level

No Education Listed

Number of Employees

5,001-10,000 employees

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