Damjan Draskovic
Summary
Enterprise System Administrator specializing in secure, resilient, and highly available IT infrastructure for mission-critical environments. Experienced in Active Directory, Windows Server, Microsoft Entra ID, Hyper-V, and Cisco Meraki deployments across Massachusetts and the Greater Boston area. Led 1,000+ device rollouts and multi-site infrastructure builds, improving reliability and minimizing downtime. Passionate about developing expertise in AI and cloud technologies, implementing secure authentication, automated device provisioning, and scalable cloud and endpoint management solutions to enhance operational efficiency and the modern digital workplace.
Overview
2027
2027
years of professional experience
Work History
System Administrator
Nentec Computers
Newton, MA
2021 - Current
- Architected and administered multi-site Active Directory environments across corporate and healthcare clients, designing custom GPOs and managing DNS/DHCP to strengthen security posture and optimize operational workflows.
- Executed full hypervisor platform migration from VMware ESXi to Microsoft Hyper-V, managing all phases including VM conversion, virtual switch reconfiguration, storage remapping, and post-migration validation with minimal end-user impact
- Performed a full audit of existing Group Policy Objects (GPOs), removing redundant, unused, and conflicting policies and restructuring assignments to ensure clean, predictable policy inheritance across all users and devices
- Rebuilt the Organizational Unit (OU) structure from the ground up to reflect the client's organizational layout, enabling proper delegation of control, streamlined administration, and logical separation of users, computers, and service accounts
- Established and enforced standardized GPO naming conventions, linking policies, and documentation practices — bringing the environment up to internal IT standards and ensuring long-term maintainability for ongoing managed services support
- Architected and deployed a multi-layered backup and disaster recovery strategy leveraging Veeam Backup & Replication and MSP360 Backup, establishing automated, encrypted backup jobs with offsite and cloud retention policies to meet business continuity requirements
- Led enterprise-wide Physical-to-Virtual (P2V) server migration project, utilizing Disk2VHD to convert physical host servers into Microsoft Hyper-V virtual machines - improving system redundancy, reducing hardware overhead, and increasing overall infrastructure reliability
- Led full lifecycle server infrastructure implementations for medical practices (50+ hosts), including hardware design and configuration (Dell/HP servers, RAID 1/5/10), VMware hypervisor deployment, and provision of Domain Controllers to establish secure, scalable environments.
- Engineered secure network infrastructures using Cisco Meraki firewalls and switches, configuring VLAN segmentation, site-to-site VPNs, static IP schemas, and DHCP environments across wired and wireless networks. Reduced client downtime by 25% through performance optimization and proactive configuration improvements.
- Designed and deployed a centralized Microsoft Deployment Toolkit (MDT) solution, automating Windows 11 rollout across 1,000+ devices in 150+ dental and medical practices. Implemented automated patch management and endpoint security updates using NinjaRMM, improving compliance and reducing manual intervention.
- Directed complex Active Directory and Data migrations, including FSMO role transfers and infrastructure modernization, successfully decommissioning legacy systems with zero business disruption. Implemented MFA within Microsoft 365 to strengthen identity security and ensure protection of sensitive healthcare data.
- Partnered with Dental software vendors (Dentrix, Eaglesoft, OpenDental) to deploy and integrate imaging and practice management platforms across 30+ sites, ensuring seamless network integration and regulatory compliance.
- Migrated and rebuilt SQL database infrastructure for Dental software, resolving data integrity and connectivity issues to restore system operations.
- Implemented organizational identity structure in Microsoft Entra ID by creating tenants, users, and groups to manage access efficiently.
- Provisioned and enforced Conditional Access policies in Microsoft Entra ID to secure user access and protect organizational resources.
- Assisted with device enrollment and deployment workflows using Windows Autopilot, enabling streamlined endpoint provisioning.
IT Specialist
Newton-Wellesley Hospital
Newton, MA
08.2018 - 11.2021
- Delivered enterprise-level endpoint and systems support across 1,000+ devices spanning 100+ affiliated medical practices throughout Greater Boston, maintaining high-availability technology operations in a regulated healthcare environment.
- Led large-scale Windows 10 deployment initiative across 1,000+ endpoints within a 10-month timeline, coordinating closely with clinical and administrative leadership to ensure zero disruption to patient care and operational continuity.
- Supported infrastructure expansion for 50+ new medical practice sites, deploying and configuring Cisco Meraki security appliances, enterprise switches, and structured network components to enable secure, scalable connectivity.
- Directed Epic EMR rollouts across five new clinical locations, ensuring seamless integration with existing systems and workflows.
- Played a critical role during the COVID-19 response by provisioning and securing remote-access devices for physicians and clinical teams, enabling uninterrupted patient care delivery under emergency conditions.
Education
Bachelor of Science - Computer Information Systems
University of Maine Augusta
2027
Associate of Science - Information Technology
Southern Maine Community College
2017
Timeline
IT Specialist
Newton-Wellesley Hospital
08.2018 - 11.2021
Associate of Science - Information Technology
Southern Maine Community College
System Administrator
Nentec Computers
2021 - Current
Bachelor of Science - Computer Information Systems
University of Maine Augusta