L2 Support Specialist or Subject Matter Expert

Penbrothers International; Philippines; Hybrid; PHP 600,000 - 900,000; Full time

Benefits offered by this job

Meaningful work & Growth

Employee welfare

Global reach & local impact

Job summary

Penbrothers in the Philippines seeks a Level 2 Support Specialist to deliver advanced Microsoft 365 assistance, handle escalations from Level 1, and drive root-cause resolution in a hybrid setup. You will collaborate daily with global Customer Experience and Product/Engineering teams while improving processes and knowledge bases.

The role requires strong troubleshooting, deep MS 365 knowledge, and a passion for documentation and training.

Qualifications

• Proficient in English (written and verbal).
• Strong analytical and problem-solving skills.
• Experience with service management tools (Freshdesk, Zendesk, ServiceNow) and ITIL practices.
• Advanced knowledge of Microsoft 365 services across cloud-only and hybrid infrastructures.
• Strong knowledge of Active Directory, Azure AD, and synchronization (AD Connect).
• Hands-on Exchange management in on‑premises and hybrid environments.
• Experience creating clear internal and customer-facing documentation.

Responsibilities

• Act as escalation point for Level 1, handling complex tickets to resolution.
• Diagnose and resolve advanced Microsoft 365 issues (cloud and hybrid).
• Differentiate product defects from configuration issues and coordinate with Product/Engineering.
• Develop proactive processes to prevent recurrence (KBs, training).
• Test resolved issues and provide feedback on bugs and features.
• Maintain clear communication with customers with updates and workarounds.
• Create advanced product knowledge resources and troubleshooting guides.
• Mentor Level 1 team on complex topics and best practices.

Skills

English proficiency

Analytical thinking

ITIL practices

Microsoft 365 expertise

Active Directory/Azure AD

Exchange on‑prem & hybrid

Documentation

Cross‑functional collaboration

Tools

Freshdesk

Zendesk

ServiceNow

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

Our client is the #1 Microsoft 365 management platform for IT teams who are transforming the way they run their Microsoft 365 stack. They deliver a unified approach to configuration management, delegated administration, and automated governance with capabilities far beyond native tools or point products. Organizations of all sizes choose them to command their operations, optimize tasks, refine governance strategies, and empower their workforce.

They empower organizations to achieve more with Microsoft 365. They are proud to be a Microsoft AI Cloud Partner and available in the Azure Marketplace. They are committed to working exclusively with the global network of Microsoft resellers, solution integrators, and managed service providers.

About the Role

As a pivotal member of our team, the Level 2 Support Specialist plays a crucial role in delivering advanced technical assistance within a dynamic and highly technical environment. You will handle escalated issues from Level 1, collaborate daily with our global Customer Experience and Product/Engineering teams, and drive root-cause resolution for complex Microsoft 365 scenarios. This role requires strong troubleshooting skills, deep product and M365 knowledge, and a passion for improving processes and sharing knowledge.

Work Setup:

Hybrid - 3x a week onsite in The Enterprise Center, Ayala, Makati City

Work Schedule:

Shifting Schedule covering day, afternoon, evening, and graveyard shifts to support EMEA, US, and APAC regions (9 hours per day)

What You'll Do

• Act as an escalation point for Level 1 support, owning complex or high-priority tickets through to resolution.
• Diagnose and resolve advanced technical issues involving Microsoft 365 (cloud and hybrid), Active Directory/Azure AD, and advanced configuration scenarios.
• Differentiate between product defects, configuration issues, and usage questions, and work closely with Product and Development teams on confirmed defects.
• Identify and elevate priority issues, and help design and implement proactive processes to prevent recurrence (e.g., KB updates, training).
• Assist in testing resolved issues and bug fixes prior to release, providing feedback to Product and Engineering.
• Maintain ongoing, clear communication with customers on complex issues, including interim updates, workarounds, and next steps.
• Develop and maintain advanced product knowledge resources/documentation such as in-depth How To guides, troubleshooting playbooks, and user manual updates.
• Occasionally build training materials and coach the support team to ensure consistent, high-quality service on more complex topics.
• Adhere to the organization's information security policy and requirements, including incident reporting, access controls, and secure handling of customer information.
• Provide guidance and informal mentoring to Level 1 team members on complex technical topics and best practices.

What You Bring

• Proficient in English (written and verbal).
• Strong analytical and problem-solving skills, with proven experience distinguishing development issues from configuration/support issues.
• Solid experience with service management tools (e.g., Freshdesk, Zendesk, ServiceNow, or similar) and ITIL-oriented practices.
• Advanced knowledge of Microsoft 365 services across cloud-only and hybrid infrastructures (e.g., Exchange Online/On-Prem, SharePoint, Teams, Entra ID/Azure AD).
• Strong knowledge of Active Directory, Azure Active Directory, and synchronization processes (e.g., Microsoft AD Connect).
• Hands-on experience with management tasks in Microsoft Exchange in on-premises and hybrid environments.
• Experience creating clear internal and customer-facing documentation for complex technical topics.
• Experience collaborating with Product/Engineering teams on escalations, bug reports, and feature clarifications is a plus.
• Project management skills and experience leading small initiatives (e.g., tooling improvements, documentation projects, training rollouts) are a plus.

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.