Support Specialist

Penbrothers; Philippines; Remote; PHP 600,000 - 1,200,000; Full time

Job summary

Penbrothers International is seeking an IT Support Specialist to serve as a client-facing technical authority. You will diagnose and resolve advanced issues across Windows, macOS, cloud services, and mixed environments while overseeing end-to-end resolutions and proactive improvements.

You will work remotely with flexible hours after an initial Eastern Time aligned period, supporting multiple clients and collaborating in a cross-functional team to deliver high-quality service and customer

Qualifications

• 5+ years in MSP or fast-paced multi-client IT support
• Excellent troubleshooting across systems, networking, cloud services, and security fundamentals
• Strong customer-first mindset with ability to explain complex tech to non-technical users
• Proactive in improving processes, documentation, and tooling

Responsibilities

• Serve as client-facing technical authority for complex support needs
• Diagnose and resolve difficult issues across Windows, macOS, Microsoft 365, Google Workspace, and hybrid environments
• Own issues end-to-end with in-depth investigation and follow-up
• Provide advanced networking support including firewalls, VPNs, DNS/DHCP, Wi‑Fi, and routing
• Collaborate with teammates in a non-tiered support structure with shared ownership
• Participate in migrations, deployments, security initiatives, and upgrades
• Identify recurring issues and recommend automation or tooling improvements
• Maintain clear documentation and contribute to internal knowledge resources

Skills

Troubleshooting

Customer-facing communication

Ownership

Process improvement

Security fundamentals

Tools

NinjaOne

HaloPSA

Datto

Acronis

Sophos

Avanan

Arctic Wolf

Meraki

UniFi

SonicWall

Jamf

Job description

About Penbrothers

Penbrothers is an HR & remote talent management partner and one of the fastest-growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes.

About the Client

The Client is a leading managed service provider (MSP) and IT support company.

About the Role

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.

What You Bring

• 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.

Our Hiring Process & AI Disclaimer:

We use AI tools to streamline our application process—including an initial conversation with an AI Interviewer. All hiring decisions are made entirely by humans: our Talent Acquisition team guides your full candidate journey and makes all evaluation decisions.

You are welcome to use AI for CV refinement and research, but real-time AI assistance during interviews or skill assessments is strictly prohibited to ensure an authentic evaluation.

Read our full AI Disclaimer to learn more

What You'll Get

At Penbrothers, we are obsessed with creating positive employee experiences. Here you'll find an environment that nurtures learning and provides opportunities for growth. You'll have the opportunity to make an impact on fast-growing startups and dynamic companies.

• 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.