MIKE TERRANA
Professional Profile
Hands-on IT systems engineer with 15+ years modernizing and securing Microsoft 365, Azure, identity, endpoint, and hybrid infrastructure across multiple companies. Technical lead for complex tenant consolidation and cloud-first transformation, with strengths in Entra ID, Conditional Access, Exchange Online, Intune, Microsoft security and compliance, and PowerShell automation. Expanded cross-platform engineering experience through independent, AI-assisted development of secure, self-hosted applications involving containerization, CI/CD, cloud identity, API integration, and operational monitoring.
Selected Technology Leadership & Transformation Highlights
- Technical lead for a four-to-one Microsoft 365 tenant consolidation spanning approximately 1,000 mailboxes, 650 OneDrive accounts, 300 SharePoint sites, and 200 managed devices.
- Engineer layered Entra ID security across production tenants using Conditional Access, MFA, FIDO2, Windows Hello for Business, RBAC, guest governance, and risk-based controls.
- Helped move a traditional multi-office environment from Active Directory, VMware, and site-to-site VPNs toward Azure, Entra ID, Intune, and cloud-first operations; transitioned one tenant to cloud-only identity.
- Build and maintain PowerShell automation for Microsoft 365 operations, tenant migrations, reporting, permissions, and endpoint management, using preflight validation and staged execution.
- Manage Microsoft licensing, Azure subscriptions, CSP/vendor relationships, and procurement across companies, with prior purchasing authority of approximately $50,000 per month.
Core Technology & Leadership Capabilities
Microsoft 365 & Modern Workplace Exchange Online • Teams / Teams Phone • SharePoint Online • OneDrive • Microsoft 365 Copilot • Power Automate • Licensing / CSP
Identity, Security & Compliance Entra ID / Active Directory • Conditional Access • Identity Protection • MFA / FIDO2 / Windows Hello for Business • RBAC / B2B • Defender • Purview / DLP • Retention / Audit • SPF / DKIM / DMARC
Azure, Cloud & Hybrid Infrastructure Azure VMs / VNets / NSGs • Front Door / WAF • Azure Files / Backup • Recovery Services • Monitor / Log Analytics • Cost Management / Reservations • Key Vault • VPN • VMware ESXi • Windows Server • Google Cloud
Endpoint & Network Management Intune / MDM • Windows Update for Business • BitLocker • Defender / Sophos • Level RMM • Group Policy • FortiGate • Ubiquiti • Switching / Wireless • DNS / DHCP
Tenant Migration & Automation Quest On Demand Migration • Cross-tenant Exchange / OneDrive / SharePoint • PowerShell • Microsoft Graph • PnP PowerShell • C# / .NET • Migration Validation
Self-Hosted Infrastructure & DevOps (Independent Projects) Synology NAS • Docker / Compose • Cloudflare Tunnel / Access / Pages • Tailscale • Git / GitHub • GitHub Actions / GHCR • CI/CD • Docker Secrets / CSP / HSTS • Backups / Rollback
Application Technologies (Independent Projects) Python / FastAPI / SQLAlchemy / Alembic • Node.js / Express • React / TypeScript / Vite / PWA • HTMX • PostgreSQL / SQLite • REST APIs / Webhooks • Playwright / Vitest / pytest • OCRmyPDF / Tesseract • Eleventy
AI Engineering & Application Identity (Independent Projects) Claude Code • Codex • ChatGPT • MCP / agent routing • OAuth 2.1 • MSAL.js / Entra OIDC • OpenTelemetry
Technology Operations & Cross-Platform Systems Multi-company IT Operations • Vendor / CSP Management • Cost Optimization • Procurement • Executive Support • RingCentral • Salesforce
Professional Experience
Senior hands-on technical resource supporting Microsoft 365, identity and security, Azure/hybrid infrastructure, endpoint management, networking, automation, and escalation for 700+ users across multiple companies.
- Lead the four-to-one Microsoft 365 tenant consolidation across Exchange, OneDrive, SharePoint, Teams, identity, and endpoints, coordinating Quest ODM, phased migrations, preflight validation, cutovers, PowerShell tooling, and stakeholder communication.
- Design and administer Entra ID controls, including Conditional Access, authentication strengths, MFA, FIDO2, Windows Hello for Business, Identity Protection, RBAC, B2B access, and governed exceptions; transitioned legacy directory synchronization to cloud-only identity for one tenant.
- Strengthen Microsoft 365 and email security through Defender, Purview, audit/retention, anti-phishing controls, Exchange authentication hardening, SPF / DKIM / DMARC, and incident-oriented remediation.
- Operate Azure VMs, networking, storage, backup/recovery, monitoring, and VPN while reducing on-premises dependencies; manage Intune enrollment, compliance, application deployment, Windows updates, BitLocker, endpoint security, and Level RMM.
- Assessed Azure Front Door/WAF, infrastructure lifecycle, cloud spend and reservations to prioritize remediation.
- Engineer reusable PowerShell, Microsoft Graph, and PnP automation for Microsoft 365 administration, SharePoint governance, tenant migrations, reporting, software deployment, and endpoint management, with staged validation to reduce production risk.
- Built a documentation-grounded Claude Code skill for Microsoft 365 administration, using Graph for read-only tenant audits and approval-gated changes.
- Shipped a C#/.NET self-service Office/OneNote cache-repair tool requiring no administrative access.
- Manage Microsoft licensing, Azure subscriptions, CSP/vendor relationships and procurement; audit cloud billing and forecasts.
Provided discreet, responsive technology support to senior leadership across corporate, remote, and private environments.
- Supported enterprise networking, secure remote access, executive devices, multi-rack infrastructure, distributed Crestron / Sonos AV, security systems, and guest connectivity across complex properties.
- Managed Teams Rooms and meeting technology, device procurement and deployment, presentations, travel connectivity, and time-critical escalations with minimal disruption.
Own technology strategy and day-to-day IT operations for a 20-person, nationally distributed business.
- Administer Microsoft 365, Entra identity, RingCentral, Salesforce, collaboration, telephony, licensing, access control, and endpoint security.
- Manage headquarters and remote endpoints, networking/firewall/Wi-Fi/VPN, MFA, backup/recovery, vendor selection, procurement, budgets, and renewals.
- Built a Teams directory using MSAL.js/Graph with live presence; modernized the company website and advisor assessment.
Selected Independent Engineering Projects
Architected and maintain secure, self-hosted applications with Claude Code, Codex, and ChatGPT, using model-aware development, automated testing and controlled release practices.
- Beacon - job-search PWA: Deployed React/TypeScript and Node/Express application integrating employer ATS sources, forwarded alerts, Entra sign-in with server-side authorization, verified document generation and OAuth 2.1/MCP connectivity.
- Tally - household finance PWA: Built a release-ready React/TypeScript and FastAPI/SQLAlchemy/PostgreSQL platform with isolated workspaces, immutable bills, offline OCRmyPDF/Tesseract processing and validated Cloudflare Access tokens.
- FFCopilot / Signal - fantasy analytics: Shipped Python/FastAPI/HTMX/SQLite service integrating ESPN/Yahoo and external data for lineup, waiver and survivor analytics, with automated tests and staged releases.
- Infrastructure and delivery: Zero-trust Synology NAS hosting with Docker Compose, Cloudflare Tunnel/Access, Entra SSO and private Tailscale access; GitHub Actions/GHCR CI/CD, backup, rollback and gated deployment.