Alex Winnick
Microsoft 365 Administrator
Carol Stream
Summary
Results-driven Systems Administrator with 10+ years of experience delivering desktop and cloud-based solutions across both small businesses and global enterprises. Proven track record of leading complex, cross-functional projects with international reach. Recognized for expert-level problem-solving in business-critical applications and a commitment to delivering exceptional service. Adept at troubleshooting, stakeholder communication, and fostering collaborative team environments.
Overview
11
11
years of professional experience
Work History
Systems Administrator II – Enterprise Collaboration – Microsoft 365
ALDI
04.2021 - Current
- Led enterprise-wide deployment of Microsoft 365 services for over 30,000 ALDI store employees, driving digital transformation and operational efficiency.
- Directed migration and implementation of Office 365 Apps for Enterprise across 5,000+ users, ensuring seamless adoption and minimal disruption.
- Championed Copilot rollout and case study initiative for 100+ users, collecting feedback and delivering a comprehensive cost-benefit analysis to Board Members.
- Managed Microsoft Teams administration, optimizing call performance and configuring policy deployments to support secure, scalable collaboration.
- Oversaw M365 Admin Center operations, including Entra ID and Azure AD administration, ensuring robust identity and access management.
- Designed, deployed, and maintained software packages, patches, OS tasks, and SQL queries using IVANTI Management Suite to support enterprise IT needs.
- Provided Tier 3 support for Microsoft 365 services and applications, resolving complex issues and serving as escalation point for technical teams.
- Served as Problem, Incident, and Knowledge Manager within ServiceNow, streamlining ITSM processes and enhancing team efficiency through structured knowledge management.
Systems Administrator – Digital Workplace
ALDI
11.2018 - 04.2021
- Led migration of 4,000 devices from Windows 7 to Windows 10, and continue to oversee annual Windows OS version upgrades using IVANTI Management Suite.
- Directed biannual BIOS and driver update cycles for Dell client devices, including rigorous testing and phased rollouts to ensure stability and compatibility.
- Led end-to-end implementation of VPN and firewall transition from Checkpoint Encryption to FortiNet, enhancing network security and performance.
- Spearheaded deployment of Store Wi-Fi on client devices across 2,600+ ALDI locations, enabling seamless laptop connectivity for in-store employees.
- Managed testing, coordination, and distribution of Jabra headsets to 4,000 ALDI employees, improving communication and productivity.
- Utilized JIRA, ServiceNow, and Smartsheet to track project milestones and manage international incidents with precision and transparency.
- Served as primary liaison with national and international business stakeholders, ensuring clear communication and successful project execution from planning to delivery.
- Administered CryptoPro Secure Disk for BitLocker, maintaining data encryption standards across enterprise devices.
- Conducted compatibility testing for Dell client hardware, BIOS, drivers, and Windows 10 OS releases to validate performance and reliability.
- Developed and deployed software packages, OS tasks, and SQL queries within IVANTI Management Suite to support enterprise IT operations.
- Provided Tier 3 support for ALDI client devices, including Microsoft Office applications, login scripts, OS management, and Group Policy troubleshooting.
Senior IT Service Desk Specialist
Assurance Agency (Marsh & McLennan Agency LLC)
04.2018 - 11.2018
- Implemented, configured, and deployed Windows 10 to over 500 machines using SCCM, ensuring a smooth and standardized rollout across the organization.
- Supported Office 365 migration from on-premises to cloud, contributing to project implementation and post-migration support as the designated Office 365 Administrator.
- Served as primary coordinator for Windows 10 user hand-offs, managing both in-office and remote communications, scheduling, and onboarding.
- Utilized SCCM to build and manage deployment infrastructure, including task sequences, driver imports, application packaging, and creation of device/user collections.
- Managed Active Directory operations, including user and machine account configuration, OU structuring, and maintenance of security matrices for access control.
- Acted as lead point of contact and mentor for Service Desk team, providing guidance and technical escalation support.
- Collaborated with Infrastructure, Security, and Network teams on key initiatives such as:
- Installation and configuration of Meraki access points and Cisco switches
- Deployment and maintenance of Carbon Black antivirus
- Implementation of LAPS for Windows 10
- Optimization of SCCM environment for long-term scalability - Developed and maintained internal knowledge base for the Service Desk team and managed SharePoint document libraries within Office 365.
IT Service Desk Specialist
Assurance Agency (Marsh & McLennan Agency LLC)
06.2016 - 04.2018
- Consistently resolves ServiceNow tickets with minimal reopens or escalations, maintaining high first-contact resolution rates.
- Validates issue resolution through thorough testing, ensuring long-term stability and user satisfaction.
- Executes hands-on desktop support, including software installations/upgrades, hardware setup, system configuration, and file backup implementation.
- Responds promptly to Service Desk inquiries via phone and email, delivering courteous and effective support to end users.
- Builds strong rapport with Service Desk customers, actively listening and gathering detailed information to diagnose issues accurately.
- Manages diverse technical tasks and projects, demonstrating adaptability and initiative across changing priorities.
- Takes ownership of new and unique requests, ensuring timely and effective resolution beyond standard procedures.
- Provisions and de-provisions user accounts in Active Directory, Exchange Server 2013, and internal systems, maintaining appropriate access and permissions.
IT Support Technician
Tranzact Technologies
09.2014 - 06.2016
- Diagnosed and resolved issues across desktop systems, applications, networking, and infrastructure, ensuring minimal downtime and optimal performance.
- Managed user accounts in Active Directory, supporting both current and former employees under the guidance of the IT Manager.
- Monitored and applied WSUS updates on local and remote servers running Windows Server 2008 R2 and 2012 to maintain system security and compliance.
- Maintained detailed logs of system issues and backup activities, supporting audit readiness and disaster recovery protocols.
- Oversaw system backups and contributed to project-based tasks, including new workstation builds and deployments.
- Communicated with end users via email and in person, accurately documenting issues and verifying resolutions to ensure user satisfaction.
- Resolved incidents and performed software and hardware upgrades, enhancing system functionality and user experience.
- Maintained and supported network printers and scanners, including IP configuration, maintenance kit replacements, and toner cartridge management.
Education
Bachelor of Science - Operations Management, Computer Information Systems
Elmhurst College
Elmhurst, Illinois06.2016
Skills
- M365 Administration
- Windows 10/11 Administration
- JIRA
- Service Now
- Smartsheet
- IVANTI LANDesk
- SCCM
- SQL
- PowerShell
- Problem Manager
- Incident Manager
- Knowledge Manager
- Active Directory
- Networking tools / commands
- Network troubleshooting
- Software installation
Timeline
Systems Administrator II – Enterprise Collaboration – Microsoft 365
ALDI
04.2021 - Current
Systems Administrator – Digital Workplace
ALDI
11.2018 - 04.2021
Senior IT Service Desk Specialist
Assurance Agency (Marsh & McLennan Agency LLC)
04.2018 - 11.2018
IT Service Desk Specialist
Assurance Agency (Marsh & McLennan Agency LLC)
06.2016 - 04.2018
IT Support Technician
Tranzact Technologies
09.2014 - 06.2016
Bachelor of Science - Operations Management, Computer Information Systems
Elmhurst College