[Hiring] Support Specialist @Penbrothers

Role Description

As an IT Support Specialist, you’ll be a primary, client-facing point of contact, responsible for expertly resolving advanced technical issues, driving long-term and systemic fixes, and continuously improving how support is delivered. This is not a call-center or ticket-churn role - it is a role for an engineer who excels at both technical mastery and client relationship management. You’ll work across multiple client environments, communicate proactively and clearly with stakeholders, and take complete ownership from initial request through resolution and follow-up. Success in this role requires both advanced troubleshooting capability and excellent customer-facing judgment and empathy.

Work hours:

• First 90 days: 9:00 AM – 6:00 PM Eastern Time (Night shift in the Philippines).
• Post-90 days: Flexible/ideal shift adjusted to 1:00 PM – 10:00 PM / 2:00 PM – 11:00 PM ET.

Work set-up:

• Remote

What you’ll do:

• Serve as a trusted, client-facing technical authority for more complex support needs, managing both the technical solution and the client's experience.
• Expertly diagnose and resolve difficult, non-routine issues across Windows, macOS, Microsoft 365, Google Workspace, and mixed cloud/on-prem environments.
• Own issues end-to-end including in-depth investigation, root cause resolution, meticulous documentation, and consistent client communication.
• Provide advanced support for networking components such as firewalls, switches, VPNs, DNS/DHCP, Wi-Fi, and routing.
• Partner with teammates in a non-tiered support structure that values cross-functional collaboration and shared ownership.
• Participate in client projects including migrations, deployments, security initiatives, and system upgrades.
• Identify recurring issues and recommend automation, tooling improvements, or process changes.
• Maintain clear, accurate documentation and contribute to internal knowledge resources.

Qualifications

• 5+ years of demonstrable experience in an MSP or fast-paced, multi-client, multi-site IT support environment.
• Exceptional troubleshooting skills across systems, networking, cloud services, and security fundamentals (ability to diagnose problems beyond level 2 support).
• Proven, customer-first mindset with outstanding interpersonal skills and the ability to communicate complex technical concepts clearly and calmly to non-technical users and C-level stakeholders.
• High level of comfort diagnosing unfamiliar technologies through logic, research, and experimentation.
• High ownership mentality - taking complete ownership from initial request through resolution.
• Proactive approach to improving processes, documentation, and tooling.

Nice to Have

• Certifications (Microsoft, Cisco, CompTIA, etc.)
• Experience with NinjaOne, HaloPSA, Datto, Acronis, Sophos, Avanan, Arctic Wolf, Meraki, UniFi, SonicWall, Jamf.

Benefits

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.