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
- Client Support
- Hybrid / Remote
- Full-time
Help Desk Technician
Be the first response for client tickets, troubleshooting issues end to end.
You will work the front line of the DSS service desk, taking client requests from first contact through resolution. The role suits someone who enjoys steady troubleshooting, clear communication, and building the habits that grow into a systems or security career.
Responsibilities
- Answer inbound calls, emails, and portal tickets, then log them accurately in the PSA
- Troubleshoot Windows, macOS, printer, and connectivity issues for end users
- Handle account tasks such as password resets, mailbox changes, and license assignment
- Escalate complex issues with clean documentation so engineers can pick up quickly
- Follow up with clients until tickets are resolved and confirm satisfaction before closing
Requirements
- 1+ years in a help desk, desktop support, or customer-facing IT role
- Comfortable supporting Microsoft 365, Windows 10/11, and common business applications
- Clear written and verbal communication with non-technical users
- Strong follow-through on ticket queues, SLAs, and daily prioritization
- Eligibility to work in the posted region without sponsorship
Preferred qualifications
- Exposure to ticketing platforms such as ConnectWise, Autotask, or HaloPSA
- Familiarity with Active Directory, Azure AD, and basic network troubleshooting
- CompTIA A+, Network+, or similar coursework and certifications
Submit your application
Share your background and the systems you have supported. We review every submission and respond when there is a clear fit.