Resume

MIKE TERRANA

IT Infrastructure & Microsoft 365 Lead
Multi-Company Technology Operations | Identity & Security | Cloud & Endpoint Management | Modernization & Automation

Professional Profile

Hands-on IT Infrastructure and Microsoft 365 technical lead with 15+ years of experience securing, modernizing, and consolidating technology environments across multiple companies. Deep expertise spanning Microsoft 365, Entra ID and identity management, Azure and hybrid infrastructure, Intune endpoint management, Microsoft security and compliance, networking, and PowerShell automation, complemented by cross-platform experience across Google Cloud, RingCentral, and Salesforce.

Technical project lead for complex Microsoft 365 initiatives, combining deep technical expertise with practical business judgment across security, operational impact, scalability, user experience, and cost. Experienced in multi-company technology operations, vendor and CSP management, licensing strategy, technology procurement, infrastructure modernization, and high-trust executive support requiring discretion, confidentiality, and minimal business disruption.

Selected Technology Leadership & Transformation Highlights

  • Technical project lead for consolidating four independent Microsoft 365 tenants into one: approximately 1,000 mailboxes, 650 OneDrive accounts, 300 SharePoint sites, and 200 managed devices.
  • Design and administer layered identity security across two production tenants, including 12 active Conditional Access policies, passwordless authentication (FIDO2, Windows Hello for Business), RBAC, and risk-based controls.
  • Helped transform a traditional multi-office environment (on-premises servers, VMware, Active Directory, site-to-site VPNs) into a distributed cloud-first model built on Azure, Microsoft 365, Intune, and modern identity services.
  • Develop and maintain 31 production PowerShell scripts automating administration, migration, reporting, and endpoint management, using controlled validation and staged execution to reduce production risk.
  • Manage Microsoft licensing, Azure subscriptions, and CSP/vendor relationships across multiple companies, with prior purchasing authority of approximately $50,000 per month.

Core Technology & Leadership Capabilities

Microsoft 365 & Modern Workplace Microsoft 365 Administration • Exchange Online • Teams • SharePoint Online • OneDrive • Copilot • Power Automate • Microsoft 365 Licensing

Identity, Security & Compliance Entra ID • Active Directory • Conditional Access • MFA • Authentication Strengths • FIDO2 • Windows Hello for Business • RBAC • Entra B2B / Guest Access • Identity Protection • Defender • Purview • DLP • Secure Score • Audit & Retention • SPF / DKIM / DMARC • Hybrid Identity

Azure, Cloud & Hybrid Infrastructure Microsoft Azure • Azure VMs • Virtual Networks • Network Security Groups • Azure Storage / Files / Backup • Recovery Services • Azure Monitor • Log Analytics • Azure VPN • VMware ESXi • Windows Server

Endpoint, Network & Device Management Microsoft Intune • MDM • Application Deployment • Windows Update for Business • BitLocker • Defender / Sophos • Level RMM • Group Policy • FortiGate Firewalls • VPN • Switching • Wireless • DNS / DHCP

Automation, Migration & Modernization PowerShell • Quest On Demand Migration • Microsoft 365 Tenant Consolidation • Identity / Exchange Migration • OneDrive / SharePoint Migration • Endpoint Migration • Cloud-First Modernization • Technical Validation & Troubleshooting

Business Applications & Cross-Platform Technologies RingCentral • Salesforce • Google Cloud Billing & API Configuration • Google Workspace

Technology Leadership & Business Operations Multi-Company Technology Operations • Technical Project Leadership • Vendor & CSP Management • Licensing Strategy • Technology Evaluation & Procurement • Cost Optimization • Stakeholder Coordination • Executive Technology Support • Documentation • User Training & Adoption

Professional Experience

PRESENCE MARKETING | Chicago, IL
Systems Administrator | August 2019 – Present

Senior hands-on technical resource supporting Microsoft 365, identity and security, endpoint management, Azure/hybrid infrastructure, networking, automation, and escalated IT operations across Presence and multiple affiliated operating companies.

  • Lead complex Microsoft 365 initiatives across multi-company environments, balancing centralized technology standards with company-specific security, licensing, access, and operational requirements.
  • Serve as internal technical project lead for consolidation of four Microsoft 365 tenants into a single consolidated tenant, coordinating phased migrations, CSP/Quest ODM activities, identity and resource preparation, endpoint migration and Intune enrollment, PowerShell automation, validation, troubleshooting, stakeholder communication, and cutover support.
  • Design and administer Microsoft Entra identity and security controls, including 12 active Conditional Access policies across two production tenants, dynamic/security groups, MFA, Authentication Strengths, FIDO2, Windows Hello for Business, RBAC, guest access, risk-based controls, hybrid identity, and governed executive/service-account exceptions; proactively identify and remediate security gaps across Microsoft 365.
  • Helped transform a traditional multi-office hybrid environment into a distributed cloud-first model, reducing legacy infrastructure dependencies while expanding Microsoft 365, Entra ID, SharePoint, Teams, Intune, and Azure services; administer Azure VMs, networking, storage/files, backup/recovery, monitoring, VPN, and cloud identity integration; additionally manage Google Cloud billing and API configuration supporting an internal production application.
  • Support endpoint modernization through Microsoft Intune, including device enrollment, application deployment, compliance, Windows Update for Business, BitLocker, Windows Hello, endpoint protection, Level RMM, and production-readiness validation.
  • Develop and maintain 31 production PowerShell scripts supporting Microsoft 365 administration, reporting, migrations, SharePoint permissions, endpoint management, software deployment, and operational support, emphasizing validation, controlled execution, and production risk reduction.
  • Manage Microsoft licensing, Azure subscriptions, CSP/vendor relationships, renewals, technology evaluations, and purchasing recommendations across multiple environments; identify cost-saving opportunities and help implement platform/vendor transitions based on security, functionality, operational value, and cost.
  • Serve as an escalation resource within IT operations supporting 700+ users across multiple companies, resolving advanced Microsoft 365, Azure, identity, networking, infrastructure, and endpoint issues while providing technical guidance, documentation, and knowledge transfer.
RED TIGER LLC | Chicago, IL
Executive IT Consultant | January 2021 – January 2026

Provided high-trust technology support to senior executive leadership across corporate and private environments requiring discretion, confidentiality, responsiveness, and reliable operation of business-critical technology.

  • Served as a primary technical resource for executive technology, supporting corporate systems, executive devices, meetings, travel, remote connectivity, and sophisticated residential technology environments.
  • Supported enterprise-grade technology across executive properties of approximately 30,000 and 12,000 square feet, encompassing wired/wireless networking, multiple network racks, secure remote administration, distributed Crestron/Sonos AV, security systems, streaming technology, and guest connectivity.
  • Supported executive and corporate meeting environments, including Microsoft Teams Rooms, conference-room AV, presentations, collaboration platforms, and company-wide meetings; managed procurement, configuration, deployment, troubleshooting, and replacement of executive laptops, mobile devices, and related technology.
  • Provided responsive remote and on-site support for business-critical issues, including travel, evening, and weekend needs, maintaining secure access, clear communication, confidentiality, and minimal executive downtime.
TERRANA GROUP LLC (family business) | Chicago, IL
Chief Information Officer | 2008 – Present

Own technology strategy and day-to-day operations end to end for a 20-person, nationally distributed company, from platform selection and budgeting through implementation, security, and user support.

  • Administer the company's Microsoft 365, RingCentral, and Salesforce environments, including identity and access, email and collaboration, licensing, telephony, and CRM user management.
  • Manage endpoints, networking, and security for Chicago headquarters and remote staff across the U.S., including device procurement and lifecycle, firewall/Wi-Fi/VPN, MFA, and backup/recovery.
  • Set technology direction and manage vendor relationships, licensing renewals, and purchasing, evaluating platforms on security, functionality, and cost.