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Resume · Phoenix, AZ · Updated July 2026

Steve Ross

Digital workspace and infrastructure architect turned engineering leader. A decade of endpoint, identity, and EUC at health-tech, investment-bank, and e-commerce scale — with production AI built on top. VMware Certified Professional in, literally, Digital Workspace.

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10 yrs
in enterprise IT — health-tech, banking, e-commerce.
$420K/yr
in licensing retired by one backup automation.
3,000
endpoints migrated — AD → Entra ID, Workspace ONE → Intune.
2,600
Macs in Jamf under management, today.
The receipts

Where the decade went.

The RealReal · 2021 — present
Staff, Systems Engineer (Architect)
May 2024 — present
  • Production AI agent systems on FastMCP — Claude, GPT, and open-source models automating infrastructure operations, troubleshooting, and incident response.
  • The Microsoft stack and both endpoint fleets are mine: Intune, Entra ID, 2,600 Macs in Jamf — plus 50+ servers across on-prem, AWS, Azure, and GCP.
  • Wrote the backup automation that retired 5,000 archive licenses — roughly $420K a year, gone.
  • The unfashionable half is mine too: Windows Server, WSUS, KMS, ADCS, WDS. The stack you need when a network can't reach a vendor cloud to patch or activate itself.
  • Root-cause analysis on the incidents that matter, permanent fixes shipped.
  • Mentor to six engineers, no title required — one now leads Intune under my guidance, a second is on track to lead Jamf. Building the bench for both fleets I run.
Manager, IT Operations Engineering
May 2023 — May 2024
  • Lead engineer to manager overnight, mid-reduction-in-force: an 8-person team across networks, identity, systems, and endpoints. Every platform stayed up.
  • Ticket resolution improved 35%, downtime dropped, backup resilience and monitoring shipped — during the rebuild, not after it.
  • The full performance-management cycle, twice, on inherited hires. Plus budgets, license renewals, and vendor negotiations.
Lead, Endpoint Engineer
Jan 2021 — May 2022 · Oct 2022 — May 2023
  • Rebuilt the AD DS domain end to end first — broken replication topology, DNS timeouts, the cascade that came with it. You don't migrate a domain that's already lying to you.
  • 3,000 endpoints migrated: on-prem Active Directory → Entra ID, then Workspace ONE → Intune. Design, baselines, pilot, cutover, decommission.
  • Zero-touch provisioning across Windows, macOS, iOS, and Android — Autopilot, Apple Business Manager, Knox.
  • Okta ↔ Entra ID federation; routine ops automated away in PowerShell and Python.
Rebellion Defense · defense AI
Senior Solutions Architect
May 2022 — Oct 2022
  • MDM workflows and endpoint posture hardening across Windows and macOS — BYOD and mixed-ownership enrollment included.
  • Zero-touch Apple ADE enrollment on Workspace ONE; managed macOS identity via Jamf Connect.
  • Modernized the app catalog on InstallApplications and Munki.
Entelligence LLC · VMware partnership
Senior Consultant, EUC
Jan 2019 — Jan 2021
  • VMware Workspace ONE professional services for enterprises running 10K–50K endpoints — 95%+ deployment satisfaction.
  • Ran a major US investment bank's entire on-prem Workspace ONE stack: vIDM, UAG, active-active SQL — 100+ servers across prod, DR, dev, and UAT. SOC 2, banking-grade.
  • Tens of thousands of Android devices across hundreds of national branches — the link only opened for updates during set hours, so the config had to hold on its own in between. Constrained-bandwidth fleet management before anyone called it edge.
  • Architecture, capacity planning, and performance tuning at scale; trained the client teams who kept it running.
Cerner Corp · now Oracle Health
Systems Engineer
Jan 2017 — Jan 2019
  • Identity and directory services in a HIPAA environment — 1,000+ endpoints across a clinical fleet.
  • Stood up AirWatch MDM — the start of a decade in enterprise endpoint management — plus large-scale deployments and scripted automation for lab systems.
Before the decade

Started in customer service. The soft skills stuck.

$12 an hour, running between sites fixing printers. Then a hospital systems seat, where AirWatch shot me into orbit — VMware professional services, an investment bank's entire EUC stack, and everything since. Old-school internet kid underneath: BASIC in the AOL era, mIRC scripts. The curiosity never left; it just picked up a decade of enterprise on the way.

"If you sit at my table, you bring something to it. Show up and I'll take you to the moon."

How I run a team — title or not
Off the clock

Shipped solo, infrastructure to interface.

Production SaaS, built end to end on my own time. Not slide decks — running software with real users.

Complens.ai

Agentic DLP. Two brains: on-device detection — regex floor + semantic classifier in the browser — and cloud policy. Raw content never leaves the device.

Chatly ↗

The AI chat widget on this very page. One-line embed, self-training, books customers in the chat. chatly.today

Skool365

AI video coaching for sports teams — two apps, one serverless backend. H.265 media pipeline, frame-level video annotation, AI technique analysis, multi-tenant RBAC, COPPA-compliant, web + mobile.

Landly

An AI marketing platform, not a page builder — drag-and-drop sites, AI copy and imagery, contacts and deals, workflow automation, and a prospecting + outreach hub with its own Chrome extension.

Certifications & education
VCP — Digital Workspace
VMware Certified Professional. Yes, literally.
Jamf 200
Jamf Certified Tech
Cisco CCNA
Routing & switching
AAS, Computer Networking
The formal bit
The stack

Every tool has a job. These are mine.

Digital workspace & endpoint
Intune · Autopilot · Workspace ONE (Omnissa/AirWatch) · Jamf Pro · MECM/SCCM · Apple Business Manager · Knox · Defender for Endpoint · AVD · AWS/Azure WorkSpaces — Windows, macOS, iOS, Android, Linux
Identity & access
Entra ID · Conditional Access · Okta · Active Directory Domain Services (GPO, ADFS, ADCS, DNS, DHCP) · PKI · SailPoint · BeyondTrust · SAML/OAuth/OIDC · MFA/SSO · zero-trust/ZTNA
Cloud & infrastructure
AWS · Azure · GCP · VMware (vSphere, ESXi, vCenter, vSAN) · Hyper-V · Proxmox · Docker · Windows Server 2012–2025 · WSUS · KMS · WDS · MDT/WinPE · SAN/NAS · Brocade Fabric OS · Fibre Channel/iSCSI · Veeam · serverless (Lambda, Step Functions, DynamoDB)
Observability & ITSM
Datadog · Splunk · Grafana · SolarWinds · PagerDuty · Statuspage · ServiceNow · Freshworks
Security
CrowdStrike Falcon · Carbon Black · Palo Alto · Meraki · pfSense · Wireshark · VPN/IDS/IPS/WAF · data loss prevention · HIPAA · SOC 2
Automation & AI
PowerShell · Python · Bash · REST APIs · Okta Workflows · Tines · AI agent pipelines (FastMCP, Claude, GPT, local LLMs) · RAG · structured output

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