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.
We are currently seeking to add an Implementation Systems Administrator to our dedicated Projects team to support company growth. In this role, you will focus on delivering large-scale, proactive project work that extends beyond day-to-day support. You will be responsible for executing technical implementations – from discovery through delivery – ensuring projects are completed on-time and within budget.
Your work will directly improve client environments by enhancing security, stability, and standardization while enabling our Service Team to deliver world-class ongoing support.
Responsibilities:
- Participate in project kickoff discussions, contributing to expectations, risks, and technical approach
- Execute assigned project work in alignment with approved Statements of Work (SOWs), ensuring delivery within scope, timeline, and budget
- Deliver hands-on technical implementations across client environments, including infrastructure upgrades, migrations, and system deployments
- Provide post go-live support for project cutovers to ensure stability and optimal client experience
- Track project issues and contribute to post-project debriefs, including lessons learned and process improvement recommendations
- Take ownership of assigned project deliverables through completion and transition to the Service Team
- Draft and send client-facing project status updates
- Communicate effectively with clients and internal teams regarding project progress, upcoming changes, outages, and impacts
- Collaborate with third parties, including co-managed environments and vendors, to complete project tasks
- Maintain thorough and accurate documentation of all project activities, tools, and client environments
- Enter daily time tracking, documentation, and expenses within required systems (e.g., ConnectWise)
- Prepare for and participate in weekly project status check-ins
- Identify and raise risks, blockers, and dependencies impacting project delivery
- Contribute to team discussions and problem-solving in weekly meetings
Requirements
- 3-5 years of experience in a similar level role within a project or support divisions
- Strong diverse reactive IT support experience is required
- Experience and ability to independently complete the following project types
- Email Migrations (Various Platforms to M365)
- Server Builds and Migrations (File Server, Domain Controller, Application Servers)
- Network Upgrades and Cross Platform Migrations
- Hypervisor Replacements and Migrations (VMware, Hyper-V)
- Workstation Lifecycle Replacement Initiatives
- Office Moves and net new office build-outs
- Security Stack Deployments (e.g. MDR, SIEM)
- Application Deployments (CRM, ERP, etc.)
- Exceptional Documentation and Communication Skills
- Ability to efficiently handle multiple tasks and collaborate effectively within a fast-paces, client-oriented team
- Self-motivated with the capability to work independently with minimal supervision.
- Highly organized with a keen attention to detail.
- A current and valid US driver's license
- Any Degree in relevant technology field is considered a plus
- Certifications such as the following are considered a plus
- MCSA
- VCP
- CCNA
- Solution-based certifications (E.g. MDM) are considered a plus
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
- 3-5 years of experience in a similar level role
- Strong diverse reactive IT support experience
- Experience completing email migrations to M365
- Experience with server builds and migrations
- Exceptional documentation and communication skills
- Self-motivated with capability to work independently
- A current and valid US driver's license
- Any Degree in relevant technology field
- Certifications such as MCSA, VCP, CCNA
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.
