The work
Modern technology, real environments
Production systems that people depend on to see patients, run a plant, or keep a municipality online — not a sandbox and not a ticket queue for password resets.
Careers at DSS
Build technology that businesses actually depend on.
Medical practices, state agencies, municipalities, and growing companies run on the environments we manage. When something we built holds up at 2am, somebody gets to keep working — and when it does not, we are the ones who answer. That is the job.
Twenty years in, across IT operations, cybersecurity, and AI, in New York and Florida.
The role
What you would be working on
Security
A cybersecurity practice, not a checkbox
Detection and response, identity, email, vulnerability management, incident response, and compliance work against HIPAA and CJIS requirements that get audited.
Infrastructure
Cloud and infrastructure at depth
Microsoft 365 and Azure tenants, migrations, hybrid networks, and the backup and recovery design behind them. You will own environments end to end.
Applied AI
AI with the controls on
Private assistants, retrieval that respects permissions, workflow automation, and agents scoped with human approval. Applied AI, governed — not a demo.
Progression
Room to move
Engineers here grow across practices rather than up a single ladder — help desk into infrastructure, infrastructure into security, security into strategy.
Training
Training that keeps going
Continuous advanced training and certification, because the platforms move and the threats move faster. It is part of the job, not something you do on a weekend.
The team
A team, not a bench
Core support, engineering, and security are DSS employees, which means you own your clients and you know the people you escalate to by name.
Where
New York and Florida
Three offices across two states, with remote and onsite work in both regions.
- Westbury
- Roslyn Heights
- Pompano Beach
- IT Operations
- Hybrid / Remote
- Full-time
Systems Engineer
Support secure client infrastructure across endpoints, identity, cloud, and networks.
You will join the IT operations team supporting DSS client environments day to day. Work spans endpoint management, cloud administration, and practical escalation support for growing organizations.
Responsibilities
- Manage device lifecycle tasks including enrollment, patching, imaging, and retirement
- Administer Microsoft 365, Azure AD, and conditional access policies for client tenants
- Monitor infrastructure health, respond to alerts, and document resolutions in the PSA
- Maintain network documentation, VLAN records, and backup verification routines
- Partner with security and automation teams on hardening and operational improvements
Requirements
- 3+ years in MSP, internal IT, or infrastructure engineering roles
- Hands-on experience with Windows and macOS endpoints in production environments
- Working knowledge of DNS, VPN, firewalls, and identity fundamentals
- Ability to write clear ticket notes and client-facing status updates
- Eligibility to work in the posted region without sponsorship
Preferred qualifications
- Experience with RMM platforms such as N-able, ConnectWise, or Datto
- Familiarity with Microsoft Intune, Jamf, or similar MDM tooling
- Exposure to virtualization (Hyper-V, VMware) and basic scripting (PowerShell)
Submit your application
Share your background and the systems you have supported. We review every submission and respond when there is a clear fit.