David Gleason

About David Gleason

I’m a Lead Platform Engineer specializing in Microsoft enterprise technologies, Windows automation, and cloud infrastructure at scale. I’ve led architecture and deployment of global endpoint platforms, driving reliability, compliance, and user experience across devices.My strengths include designing secure, self-healing systems with tools like Intune, Chef, and Autopilot; automating infrastructure using PowerShell, Ruby, and Python; and building CI/CD pipelines with GitHub Actions. I’ve led major cloud migrations (AD to Entra ID), implemented Microsoft license automation saving hundreds of thousands annually, and transitioned organizations to modern, cloud-native endpoint models.I’m passionate about platform scalability, data-informed strategy, and mentoring high-impact teams. Whether it\'s automating device lifecycle, optimizing license spend, or simplifying VDI with Windows 365, I bring hands-on technical leadership and a focus on results.

Experience

1. Client Platform Engineering Lead, Windows

   Uber

   Jan 2020 — Present · San Francisco, CA, US

   Lead Platform Engineer with deep expertise in Microsoft enterprise ecosystems, cloud architecture, and infrastructure automation. I specialize in designing and scaling secure, high-performance Windows environments using tools like Intune, Chef, and CI/CD (PowerShell/Python). I bring a strong foundation in coding (PowerShell, Python, Ruby), API development, infrastructure as code, and CI/CD automation with GitHub Actions.I\'m passionate about building reliable, self-healing systems, enabling developer productivity, and leading data-driven platform strategies at scale. With a proven track record in enterprise agreement negotiation, cloud migration, and endpoint management for 50K+ devices, I combine hands-on technical depth with strategic leadership across engineering, IT, and procurement functions.Negotiated Microsoft Enterprise Agreement, reducing licensing and support costs by $3.4M.Architected Uber’s global Windows platform, enhancing automation, compliance, and UX across endpoints.Led migration from on-prem Active Directory to Entra ID, enabling a modern, cloud-first identity model.Transitioned Windows clients to cloud-native, hybrid-joined configurations—fully eliminating on-prem dependencies.Designed Microsoft license automation pipeline, cutting $313K/year in waste and enabling self-service license management.Executed a Windows 365 migration strategy, replacing AWS VDIs and saving $500K+ annually.Built scalable Chef cookbooks with built-in telemetry and remediation to enforce endpoint compliance at scale.Created custom Ruby libraries to query GraphAPI for dynamic group membership logic in config management.Delivered robust self-healing for Chef client infrastructure, ensuring consistent endpoint state and tooling compliance.Led MDM policy and provisioning strategy via Intune and Autopilot, boosting compliance and provisioning speed.Developed an end-of-life device automation system handling lock, unlock, and unenrollment workflows.

Education

• American Military University

  Bachelors, IT Management

  2009 — 2013

Skills

• High Availability
• Networking
• Active Directory
• Xp
• Windows Server
• Hardware
• Ccna
• Information Assurance
• Firewalls
• Network Security
• Windows 7
• Powershell
• San
• Disaster Recovery
• Vmware Esx
• Microsoft Sql Server
• Domain Name System (Dns)
• Tcp/Ip
• Vpn
• Vmware
• Dns
• Integration
• Cisco Routers
• Troubleshooting
• Microsoft Certified Professional
• IT Management
• Virtualization
• Dhcp
• Computer Security
• Netapp
• Wsus
• System Deployment
• Servers
• Network Administration
• Nas
• Switches
• Sharepoint
• Cisco Nexus
• Netapp Filers
• Comptia Security+