Part-Time IT & Security Engineer (Tier 2/3)

Part-Time IT & Security Engineer (Tier 2/3)
Weekend Coverage + Optional Weekday Evenings | Remote, Philippines

Sentry is a US-based managed service provider (MSP) and physical security integrator serving small and mid-sized businesses across the New York metro area. On the IT side, we manage our clients' networks, servers, Microsoft 365 environments, endpoints, and phone systems. On the security side, we design, install, and support their video surveillance and access control systems.

We do things differently from most MSPs: we don't run a Tier 1 help desk. When a client reaches us, they get a skilled engineer who takes ownership immediately, not a scripted first-tier queue or an automated phone tree. That first-contact competence is a big part of why our clients enjoy working with us, and it's why we only hire technicians at Tier 2 and above.

We're hiring part-time to cover our weekends, Saturday and Sunday, and we have additional weekday evening shifts available for the right person. Weekends and evenings are much quieter than our weekday daytime operation, so this isn't a high-pressure call queue. You'll handle the calls, emails, and tickets that do come in, owning each from first contact through resolution, and spend the rest of your time moving project work forward: deployments, configurations, maintenance windows, documentation, and backlog cleanup. Weekends and evenings are also when we can safely take systems offline for upgrades that would disrupt clients during the day, so a meaningful part of this role is planned project execution, not just reactive support.

The weekend coverage is what we're most eager to fill. If you're interested, you can also pick up one or more weekday evening shifts on top of it; the full schedule is below.

Because you'll often be our main presence outside core business hours, independence and sound judgment matter here. You won't be alone: you'll have escalation paths to senior engineers and the owner, and we take on the hardest problems as a team, but you should be comfortable owning a client environment and knowing when to escalate. The role is fully remote, and you'll be a full member of our team, not an isolated, outsourced contractor.

What You'll Do

- Handle client requests by phone, email, and ticket during your shifts, and own them from first contact through resolution
- Deliver a confident, professional experience on every interaction; clients should feel they're in good hands from the first minute
- Execute project work handed off from the weekday team: deployments, migrations, network and system configuration, and backlog items that need uninterrupted time to complete
- Run maintenance windows: patching, firmware upgrades, server maintenance, and other changes best done while clients are offline
- Administer Microsoft 365 / Entra ID (Azure AD): user and license provisioning, Exchange Online, mail flow, and email security
- Monitor and respond to RMM alerts (Atera) and manage endpoint security tools (Huntress, Bitdefender)
- Troubleshoot networks: firewalls (FortiGate), switches and access points (UniFi), VLANs, VPNs, and DNS
- Administer Windows Server, Active Directory, and Group Policy
- Manage and verify backups (Datto)
- Support VoIP systems and IP phones
- Configure, support, and troubleshoot video surveillance systems (IP cameras, NVRs, and video management software such as Hikvision, Digital Watchdog, and Speco), including secure remote access and viewing
- Administer access control systems (users, credentials, and door schedules) and troubleshoot controllers and readers
- Remotely support our field technicians during security-system installs and service calls
- Keep clear, accurate documentation for every client environment, including writing up the project work you complete
- Work alongside our AI tooling, which we use heavily across daily operations

What We're Looking For

- 3+ years of hands-on IT support experience, ideally at an MSP
- Excellent spoken and written English, with a strong customer-first attitude; you'll be the voice of our company on every call
- The confidence to own client interactions and project work independently, along with the judgment to know when to involve the team
- Self-direction: with lighter supervision outside business hours, you should be able to pick up a project, see it through, and document it without hand-holding
- Solid knowledge of Microsoft 365/Entra, Windows Server, Active Directory, and networking fundamentals
- Hands-on experience with firewalls and managed switches (FortiGate and UniFi a strong plus)
- Experience with IP video surveillance and/or access control systems, or the aptitude and willingness to develop this expertise quickly (it's a core part of what we do)
- Reliable high-speed internet with a backup connection
- A quiet, dedicated home workspace

Bonus Points

- Deep familiarity with AI tools, especially Claude, which we use extensively day to day
- Spanish-speaking ability (written and/or spoken)
- Hands-on experience with VMS platforms (e.g., DW Spectrum), access control systems, or remote video monitoring services (e.g., Immix)
- Certifications (CompTIA A+/Network+/Security+, Microsoft, Fortinet NSE, Ubiquiti, Cisco CCNA)
- PowerShell or other scripting

Work Setup

- 100% remote, based in the Philippines
- Part-time, permanent employee position, not contract work
- All hours are in US Eastern Time, which maps to an overnight or early-morning shift in the Philippines (about an hour later when the US is on standard time)

Weekend coverage, the core of this role (both days):
- Saturday, 10:00 AM to 10:00 PM ET (roughly 10:00 PM Sat to 10:00 AM Sun PHT)
- Sunday, 10:00 AM to 10:00 PM ET (roughly 10:00 PM Sun to 10:00 AM Mon PHT)
- About 24 hours per week

Optional weekday evening shifts, pick any one, two, or all three:
- Tuesday, 5:00 PM to 10:00 PM ET (roughly 5:00 AM to 10:00 AM Wed PHT)
- Thursday, 5:00 PM to 10:00 PM ET (roughly 5:00 AM to 10:00 AM Fri PHT)
- Friday, 5:00 PM to 10:00 PM ET (roughly 5:00 AM to 10:00 AM Sat PHT)
- 5 hours per shift

What We Offer

- Competitive USD pay, scaled to the shifts you take (same hourly-equivalent rate across all of them):
- Weekend coverage (Saturday and Sunday): $1,200 to $1,500 per month, based on experience
- Each weekday evening shift you add: approximately $250 to $315 per month per shift
- For reference, taking all five shifts works out to roughly a full-time load at about $1,950 to $2,450 per month
- Paid time off, pro-rated for a part-time schedule
- A stable, long-term role with real room to grow, including the potential to expand into more hours
- A supportive, AI-forward team that invests in its people

How to Apply

To apply, send your resume and a short note about your MSP and IT experience, including any hands-on work with security systems and AI tools, and let us know which shifts you're available for: weekend coverage, weekday evenings, or both.