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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 Systems Administrator (Proactive Engineer) to our Projects Team. In this role, you'll play a key part in delivering successful client outcomes by leading technical project work and serving as both a hands-on engineer and escalation point. You'll collaborate closely with clients, vendors, and internal teams to implement solutions that align with project goals and business needs.

Responsibilities:

• Lead and execute technical projects for clients, ensuring smooth delivery from kickoff through post go-live support

• Participate in project kickoff meetings to align on scope, timelines, expectations, and risks

• Complete assigned tasks as outlined in client Statements of Work (SOWs)

• Provide post go-live support to stabilize and optimize client environments

• Collaborate with third-party vendors and co-managed teams to meet project objectives

• Maintain clear and thorough documentation of systems, tools, and project processes

• Communicate proactively with clients and internal teams about changes, outages, and project impacts

• Record daily time entries, expenses, and work notes in ConnectWise

• Send weekly client-facing project status updates and participate in check-in meetings

• Engage in team discussions, project debriefs, and continuous improvement efforts

• Take on additional duties and responsibilities as assigned

Project Scope Includes:

• Hypervisor replacements and migrations (e.g., Hyper-V, VMware)

• Email platform migrations to Microsoft 365

• Server builds, upgrades, and full environment migrations

• Network infrastructure upgrades and complete overhauls

• Office IT build-outs for new or expanding locations

• Business application deployments (e.g., CRM, ERP systems)

Requirements

• 5 or more years of experience (preferred)

• Certifications such as MCSA, VCP, CCNA are a plus.

• Experience with platforms like ConnectWise, Cisco, Meraki, Datto, VMware, and Office 365 is a bonus.

• Strong communication skills are essential for success in this role.

• Ability to manage multiple tasks and collaborate effectively within a fast-paced, client-focused team.

• Enthusiastic about taking on challenges in a growing company with a diverse client base.

• Self-driven and capable of working independently with minimal supervision.

• Excellent organizational skills and strong attention to detail.

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!