Proactive Administrator

Charles IT
Chesapeake, VA

Exceptional Service. Endless Improvement. Passionate People. Honest and Forthright. These values guide everything we do, and we achieve them thanks to the diverse and collaborative efforts of our team. We are dedicated to creating a supportive environment where every team member can thrive. This includes fostering learning, professional growth, and valuing each team member’s input, all within a culture that promotes work-life balance and a strong sense of belonging.

Due to growth, we are currently seeking to add a Proactive Administrator to our exceptional team. You will be responsible for the upkeep of patching for Charles IT and our clients, liaising with the vendor.

Responsibilities

  • Execute scheduled overnight maintenance, including ESXi upgrades, firmware updates, and other planned downtime work
  • Manage and complete NOC tickets as assigned
  • Oversee system patching across client environments and troubleshoot any patching issues
  • Ensure all failed or missing patches are properly documented and assigned tickets
  • Maintain patch compliance by ensuring all patches are applied within 21 days of release
  • Collaborate with internal teams to ensure proactive system health and stability
  • Assist with additional proactive maintenance tasks and initiatives as needed

Requirements

  • 3+ years of hands-on experience in IT systems administration or a similar role (preferred)
  • Experience working with tools and platforms such as ConnectWise, Cisco, Meraki, Datto, VMware, and Microsoft Office 365 is a plus
  • Certifications such as MCSA, VCP, CCNA, or similar
  • Strong troubleshooting skills, particularly around patching and system updates
  • Excellent organizational skills with strong attention to detail
  • Ability to manage multiple priorities in a fast-paced, client-focused environment
  • Strong communication and collaboration skills
  • Self-motivated and able to work independently with minimal supervision
  • Enthusiasm for learning and growing within a rapidly expanding company

Benefits

Charles IT offers a competitive benefits program including Medical, Dental, Vision, Life, Disability, Paid Holidays, PTO, 401K, and bonuses. In addition, we offer free dry cleaning, a fully stocked break room, Friday team lunches, paid training, team-building outings every quarter, professional development and so much more!

Our Commitment to Inclusion:

Charles IT is committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, age, national origin, marital status, disability, veteran status, genetic information, sexual orientation, gender identity, or any other protected category. We welcome and encourage diverse perspectives.

The information contained in this job description is for compliance with the American with Disabilities Act (A.D.A.) and is not an exhaustive list of the duties performed for this position. Additional duties may be required.

If you’re excited about contributing your expertise to a fast-growing company that values innovation and teamwork, we’d love to hear from you!

Posted 2026-04-02

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