Senior Microsoft 365 L2 Support Specialist - Hybrid

Penbrothers International; Makati; Hybrid; PHP 360,000 - 720,000; Full time

Job summary

Penbrothers, based in the Philippines, is seeking a Level 2 Support Specialist with strong Microsoft 365 and cloud/hybrid expertise. You will handle escalations, collaborate with global teams, and drive root-cause resolution for complex scenarios.

Work Setup: Hybrid - 3x a week onsite in The Enterprise Center, Ayala, Makati City. Work Schedule: Shifting coverage across day, afternoon, evening, and graveyard to support EMEA, US, and APAC regions (9 hours/day).

Qualifications

• Proficient in English (written and verbal).
• Strong analytical and problem-solving skills.
• Solid experience with service management tools (Freshdesk, Zendesk, ServiceNow or similar) and ITIL-oriented practices.
• Advanced knowledge of Microsoft 365 services across cloud and hybrid infrastructures (Exchange Online/On-Prem, SharePoint, Teams, Entra ID/Azure AD).
• Strong knowledge of Active Directory, Azure Active Directory, and synchronization processes (Microsoft AD Connect).
• Hands-on experience with management tasks in Microsoft Exchange in on-premises and hybrid environments.

Responsibilities

• 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 upscale 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.

Skills

English proficiency

Analytical skills

ITIL knowledge

Tools

Freshdesk

Zendesk

ServiceNow

Active Directory

Azure AD

Microsoft 365 admin

Job description

Penbrothers, based in the Philippines, is seeking a Level 2 Support Specialist with strong Microsoft 365 and cloud/hybrid expertise. You will handle escalations, collaborate with global teams, and drive root-cause resolution for complex scenarios.

Work Setup: Hybrid - 3x a week onsite in The Enterprise Center, Ayala, Makati City. Work Schedule: Shifting coverage across day, afternoon, evening, and graveyard to support EMEA, US, and APAC regions (9 hours/day).