Senior Windows Administrator

This full-time Senior Windows Administrator role is based in Skopje, operating fully remote. We are seeking an experienced and highly skilled Senior Windows Administrator to architect, lead, and manage Windows and identity infrastructures across multiple client environments. In this senior-level role, you will design and implement complex server, domain, and identity solutions, establish security and governance standards, and provide expert guidance to junior and mid-level administrators. You will troubleshoot advanced technical issues, lead migrations and modernization initiatives, and collaborate closely with internal teams and clients to ensure reliable, secure, and scalable enterprise-level environments. This position requires strong bilingual communication skills to effectively document solutions, interact with customers, and lead strategic operational initiatives.

Qualifications And Responsibilities

• Architect complex Windows and hybrid identity environments.
• Lead domain modernization, migration, and consolidation projects.
• Oversee patching strategy, lifecycle management, and baselines.
• Create advanced Python automation and compliance tooling.
• Resolve high-complexity infrastructure and identity issues.
• Mentor team members and support customer technical discussions in English.
• Expert expertise in Windows Server, Active Directory, DNS/DHCP, GPO, and identity management.
• Strong background in enterprise security and infrastructure design.
• Advanced Python scripting and automation experience.
• Required: Proficiency in English and Macedonian (written and spoken).
• Availability to work Monday through Friday, remotely from 8:00 AM to 5:00 PM Eastern Standard Time (EST).

• CISSP
• CompTIA CASP+
• EC-Council CHFI
• Or equivalent professional experience

• Competitive salary range based on experience and qualifications.
• Comprehensive benefits package, including health insurance, paid time off, and ongoing professional development opportunities.
• Collaborative and supportive team environment with continuous training and growth potential.