Demo

Senior Systems Engineer (3+ years of MSP required)

Desktop Guerrillas LLC
Norwalk, CT Full Time
POSTED ON 4/5/2026
AVAILABLE BEFORE 5/3/2026

Job description

IT firm in Norwalk, CT in search of an experienced and savvy systems administrator to join our team. Our clients are mostly law, accounting and investment firms in Fairfield County and New York City. Fluency in all matters of technology, with a specific focus on security, is crucial. We employ a variety of tools to keep our clients ahead of the bad guys—this means knowing the latest solutions as well as what's on the horizon.

We're looking for a senior engineer who can walk into a project (an Intune deployment, an office move, a CRM migration) and own it start to finish. Someone who can be relied on to run independently.

Your day will split between projects and some help desk assistance, but the balance tips toward issues nobody else can solve. The core of this role is work that requires experience and judgment: projects that affect entire client environments, infrastructure that has to be right the first time.

You'll have a voice in decisions on offerings and infrastructure. We research and standardize on the best solutions across our client base (backup, security, collaboration) so you'll have deep knowledge of the systems you support and can help keep them reliable.

Because of those long-term relationships, and because our clients are the ideal size, the work extends into areas like case management system overhauls for a law firm, rethinking how an investment firm handles document security, vetting AI solutions and similar projects.


What you'll own

  • Leading projects end to end: migrations, deployments, infrastructure builds
  • Owning complex issues across servers, networking, cloud, and security that the rest of the team can't resolve
  • Building scripts and automation that improve how our team works
  • Serving as the escalation point and fount of knowledge for the rest of the team


Who you are

  • 5 years in IT, at least 3 in an MSP. You understand the pace and what it means to support clients who rely on your expertise
  • You've led projects: scoped work, communicated timelines, delivered
  • Your troubleshooting is fast, accurate, and thorough
  • You're security-minded and you communicate clearly with both technical teams and non-technical clients
  • You have experience in the core stack that’s typical at an MSP: Microsoft 365, Windows Server, networking, virtualization, security tooling.


Salary: Starting at $100,000, with higher compensation for candidates bringing advanced expertise and proven MSP experience.


Benefits: Medical/dental/vision, matching 401(k), generous PTO, flexible schedule, life insurance. Class-A office in Norwalk with fitness center, café and indoor parking.


We have a strong preference for hybrid candidates in the New York City Metro area who can make appearances at our office and meet in person with clients as needed. For the right candidate, this role can be fully remote, however.


Please respond to all screening questions. Applications that do not include responses will not be considered.


Application Questions:

  1. Have you previously worked at a Managed Service Provider (MSP)? If so, please list the company names.
  2. This position requires working in the office 2-3 days per week and traveling to client sites as needed. Our clients are primarily located within a one-hour radius of our Norwalk, CT office, though travel to locations such as New York City will also be required. Please confirm that you understand and agree to this requirement.
  3. Do you have experience managing or leading projects? If so, please describe the project and your role in it.
  4. Please provide your desired salary range for this position.


Job Type: Full-time

Pay: From $100,000.00 per year

Benefits:

  • 401(k) matching
  • Dental insurance
  • Health insurance
  • Life insurance
  • Vision insurance


Experience:

  • Managed Service Provider (MSP): 3 years (Required)
  • IT: 5 years (Required)
  • Work Location: Hybrid remote in Norwalk, CT 06854

Salary : $100,000

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