Jr. Systems Administrator

Charles IT • Middletown, CT

1d

About The Position

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 continued growth, we’re looking to add a Junior Systems Administrator to our Projects team. This role focuses on executing large-scale technical initiatives outside of day-to-day support. You’ll be responsible for implementation, discovery, documentation, and communication to ensure projects are delivered on time and within budget, helping our clients become more secure, stable, and standardized so our service team can deliver exceptional support.

Requirements

• 2+years experience in similar level role within Support Division
• Strong communication, organization, and multitasking skills
• Self-motivated, detail-oriented, and capable of working independently
• Committed to delivering results in a fast-paced, client-focused environment
• Must pass a background check and hold a valid U.S. driver's license

Nice To Haves

• Degree in a relevant technology field preferred
• Technical certifications (e.g., Servers, Security, Networking, MDM) a plus
• Experience with workstation lifecycle replacements, office build-outs and relocations and application deployments (e.g., MDR, SIEM) is a plus
• Preferred experience with: Hypervisor migrations, email migrations to M365, server builds and migrations (e.g., file servers, domain controllers), network upgrades and cross-platform migrations, and application deployments (e.g., CRM, ERP)

Responsibilities

• Participate in project kickoff meetings and discussions to align on expectations, identify risks, and define success criteria
• Execute assigned project tasks in alignment with client Statements of Work (SOWs)
• Provide post go-live support to ensure a smooth transition and optimal client experience
• Track and document issues thoroughly, contributing to process improvements and lessons learned during post-project debriefs
• Collaborate with third parties—such as co-managed partners and application vendors—to complete project tasks and provide support as needed
• Maintain clear, comprehensive documentation for all project processes, tools, and environments
• Draft and deliver client-facing project status updates
• Communicate effectively with both clients and internal teams about upcoming changes, potential outages, and overall project impact
• Enter daily time entries, expenses, and documentation into ConnectWise
• Come prepared for weekly project status check-ins
• Contribute to weekly team meetings by raising topics, solving issues, and sharing insights
• Support additional project or team-related responsibilities as assigned

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!

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed
• Number of Employees: 101-250 employees