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Field System Administrator

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 are currently seeking to add a Field System Administrator to our Stamford team! In this role, you will provide crucial support to our clients, serving as both field and escalation support, while performing the following responsibilities:

  • Provide on-site support and troubleshooting to resolve technical issues for end users.  
  • Provide support for operating systems, including Windows, Linux, and macOS.
  • Assist with software installation, configuration, and troubleshooting.
  • Perform basic networking tasks, such as IP configuration, DNS troubleshooting, and VPN setup.
  • Manage user accounts using tools like Active Directory, including account creation, modification, and troubleshooting.
  • Replace or repair hardware components such as hard drives, RAM, and printers.
  • Configure, install, and support desktops, laptops, printers, and other peripherals.
  • Collaborate with third-party vendors and IT personnel for problem resolution, including hardware repairs, software updates, and network troubleshooting.
  • Provide timely and effective support while maintaining a professional and positive demeanor.
  • Ensure accurate documentation and time entries for support activities.
  • Build and maintain strong relationships with end users, fostering trust and confidence in IT support.
  • Other duties as assigned.

  • 4 or more years of experience
  • Experience in IT support, help desk, or a related technical role.
  • Certifications such as CompTIA A+, Network+, Server+, CySA+, MS-900, and AZ-900 are a plus.
  • Hands-on experience with platforms like ConnectWise, Cisco, Meraki, Datto, VMware, and Office 365 is beneficial.  
  • Proficiency with Windows, Linux, or macOS operating systems is a plus
  • Strong troubleshooting and problem-solving skills in a fast-paced, client-facing environment.  
  • Ability to manage multiple tasks efficiently while maintaining high-quality service.  
  • Excellent and clear communication skills with the ability to explain technical issues to non-technical users.  
  • Strong organizational skills and keen attention to detail. 
  • Self-motivated, with the ability to work independently while coordinating with teams.  
  • A valid driver’s license with a clean driving record is required.
  • Willingness to travel to client sites in CT and NY. When not on site, it's required to work out of our Stamford, CT office.

 

Be a part of CT's finest and best places to work! Charles IT is a rapidly expanding IT company, recognized among Inc 5000’s fastest-growing companies, MSP’s Top 501, and Marcum’s Top Tech 40. We attribute our success to our talented team, and we’re excited to welcome new members as we continue to grow. Come join us! 

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! 
 

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Average salary estimate

$70000 / YEARLY (est.)
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$60000K
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What You Should Know About Field System Administrator, Charles IT

At Charles IT, we're on the lookout for a proactive and passionate Field System Administrator to join our dynamic team in Stamford! Our core values of exceptional service, endless improvement, and genuine collaboration create an environment that supports personal growth and work-life balance, ensuring every team member can truly thrive. In the Field System Administrator role, you will be the crucial link between us and our clients, offering on-site support, troubleshooting technical issues, and managing user accounts with tools like Active Directory. You’ll get your hands on various operating systems—think Windows, Linux, macOS—and dive into tasks like software installations, networking challenges, and hardware repairs. Your ability to communicate effectively with those who may not be tech-savvy will build trust and confidence in our services, while your strong problem-solving skills keep the wheels turning smoothly in a fast-paced environment. We’re not just about fixing tech issues; we’re about making connections and delivering timely support. If you're excited about collaborating with a team that values your input and offers opportunities for professional development, we want you to be part of our growing success story. Don’t miss out on being a part of one of Connecticut’s best workplaces, where we offer competitive benefits and a culture that celebrates diversity and inclusion. Join us at Charles IT, where your contributions make a real difference!

Frequently Asked Questions (FAQs) for Field System Administrator Role at Charles IT
What are the responsibilities of a Field System Administrator at Charles IT?

As a Field System Administrator at Charles IT, your responsibilities will revolve around providing on-site technical support and troubleshooting for end users, maintaining user accounts, and performing networking tasks. You'll be dealing with a variety of operating systems—including Windows, Linux, and macOS—conducting hardware repairs, and offering software installation assistance, all while building strong relationships with clients.

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What qualifications are required for a Field System Administrator at Charles IT?

To excel as a Field System Administrator at Charles IT, you should have at least 4 years of relevant IT support experience. Knowledge of technical roles, proficiency with operating systems (Windows, Linux, macOS), and hands-on experience with tools like ConnectWise or Office 365 are critical. Certifications such as CompTIA A+ or Network+ are also highly desired, as they showcase your commitment and expertise.

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Is travel required for the Field System Administrator position at Charles IT?

Yes, being a Field System Administrator at Charles IT involves some travel to client sites primarily in Connecticut and New York. However, when you're not out supporting our clients, you'll be working from our Stamford office, maintaining a balance that suits your work lifestyle.

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What can I expect in terms of company culture as a Field System Administrator at Charles IT?

At Charles IT, you can expect a culture that prioritizes collaboration, diversity, and professional growth. We believe in fostering a supportive environment where every team member's voice is heard, and work-life balance is respected. There are numerous team-building opportunities, and we celebrate our successes together, making it a joyful place to work.

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What benefits does Charles IT offer for Field System Administrators?

Charles IT offers a competitive benefits program for Field System Administrators that includes comprehensive medical, dental, and vision coverage, a 401K plan, paid holidays, PTO, bonuses, and unique perks like free dry cleaning and fully stocked break rooms. We also invest in our team through professional development opportunities and regular team lunches!

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Common Interview Questions for Field System Administrator
Can you explain your troubleshooting process as a Field System Administrator?

When asked this during an interview, outline your systematic approach starting from identifying the problem, gathering relevant information, and analyzing the symptoms. Discuss how you prioritize issues based on urgency and impact, and detail your interaction with clients to ensure their needs are thoroughly met throughout the process.

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What operating systems are you most comfortable supporting?

Be specific about your experience with operating systems such as Windows, Linux, or macOS. Highlight any particular projects or scenarios where your expertise was crucial, and mention any troubleshooting techniques you've developed that helped resolve common user issues.

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How do you manage your time when working on multiple client issues?

Discuss your time management strategies, such as prioritizing tasks based on severity, scheduled appointments with clients, and using tools to keep your workflow organized. Share examples where you've successfully juggled competing demands while maintaining high service quality.

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Describe a challenging technical problem you faced and how you resolved it.

Choose a specific example that reflects your problem-solving abilities. Discuss the challenge, the steps you took to identify the root cause, and how you collaborated with your team or communicated with clients during the resolution process to showcase your skills.

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How do you ensure effective communication with non-technical users?

Share your strategies for translating technical jargon into user-friendly language. Mention the importance of patience, empathy, and active listening, as well as providing clear written instructions or visual aids when necessary.

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What tools or software are you familiar with in managing IT support?

Mention specific tools like ConnectWise, Cisco, or Meraki that you've used in previous roles. Discuss how these tools have helped streamline your work processes and allow you to provide better support to your clients.

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How do you stay updated with the latest technology and trends in IT?

Explain your commitment to continuous learning through online courses, certifications, industry webinars, or tech forums. Highlight any recent learning experiences that relate specifically to the role at Charles IT, to demonstrate your proactive approach.

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What would you do if a client is unhappy with your service?

Address this by emphasizing the importance of listening to the client’s concerns, showing empathy, and taking immediate steps to rectify the situation. Discuss how you would communicate transparently and involve team members if needed to ensure the client feels valued.

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Are you comfortable working independently as well as part of a team?

Affirm your versatility in working both independently and collaboratively. Provide examples of previous situations where you thrived in both environments, clarifying how each experience enriched your capabilities as a Field System Administrator.

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Why do you want to work for Charles IT?

Communicating your interest in Charles IT by expressing admiration for their values of inclusion and professional growth is crucial. Focus on how the company’s mission aligns with your career goals and your eagerness to contribute to their success, emphasizing the positive aspects of their culture.

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April 12, 2025

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