Exceptional Service, Endless Improvement, Passionate People, and Honest and Forthright. Guided by our values, we foster a culture of growth, balance, and belonging where every team member can thrive.
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.
Skills Required
- 3+ years of hands-on experience in IT systems administration or a similar role
- Experience working with tools and platforms such as ConnectWise, Cisco, Meraki, Datto, VMware, and Microsoft Office 365
- 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
Charles IT Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Charles IT and has not been reviewed or approved by Charles IT.
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Retirement Support — An automatic 3% 401(k) contribution is offered alongside standard retirement coverage. This consistent employer contribution stands out for a company of this size.
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Equity Value & Accessibility — An employee stock ownership plan is available to provide ownership opportunities. This adds long-term value potential alongside traditional benefits.
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Career-Linked Recognition & Rewards — Training and certification incentives are tied to raises, title changes, and bonuses. Dedicated paid training time and covered exam costs reinforce a clear link between skill growth and rewards.
Charles IT Insights
What We Do
Charles IT is the Connecticut Compliance Expert, your friendly IT team focused on helping companies in highly regulated industries make their high-stakes technology work for them. Here, IT is Personal: We know that disaster recovery, cloud services, and complex compliance from HIPAA to CMCC and DFARS are only half the work. The other half is about helping people – building real relationships that deliver real results and create raving fans. Call us day or night, snow storm or hurricane: a human will answer the phone (we promise), and we will show up, on point, with a smile and a solution.
