Resume — Gerard Ostebovik

Profile

Tier 2 Azure support engineer with close to ten years at Microsoft, repeatedly selected into progressively more exclusive support teams — a founding member of Microsoft's Azure Government support team (requiring a full federal background check), the S500 Enterprise support team, and an Escalation Engineer pilot program reserved for top-performing engineers — and now building toward designing, deploying, and maintaining that infrastructure directly. Completed 14 hands-on Azure projects across networking, compute, IaC, and security, documented at ostebovik.net — production-pattern deployments built from scratch using Azure CLI, Bicep, and GitHub Actions. Deep understanding of how enterprise Azure breaks, how it should be built, and the gap between the two. AZ-104 Microsoft Certified: Azure Administrator Associate earned June 2026, with AI-103 (Microsoft Certified: Azure AI Apps and Agents Developer Associate) in progress.

Technical Skills

Azure Services

Virtual Networks NSG Azure Front Door App Gateway Load Balancer Key Vault App Service Container Apps Azure Bastion Log Analytics App Insights Entra ID Azure Policy Azure Backup Site Recovery

IaC · Automation · CI/CD

Bicep Azure CLI GitHub Actions PowerShell Bash ARM Templates Static Web Apps

Languages · Query

Python KQL SQL HTML/CSS

Support Tools · Ticketing

ZenDesk CaseBuddy MSSolve

Practices

Zero-credential architecture Managed Identity RBAC Hub-spoke topology Private endpoints WAF policy CAF naming Cost governance Enterprise support Technical writing

Experience

Tier 2 Product Support Engineer

2020 – 2025

Microsoft Corporation · Redmond, WA

Selected for Microsoft's Escalation Engineer pilot program — a small team reserved for top-performing engineers, formed once the S500 Enterprise team was fully staffed and operating as intended — handling the most complex customer-reported issues; achieved 7-day resolution for over 65% of managed cases.
Handled 5–7 managerial escalations per week, contributing to a 94% customer satisfaction rating — 10 basis points above Tier 1.
Collaborated directly with Engineering and Customer Success on issues requiring non-standard solutions, and served as the liaison between Customer Success teams and customers to deliver accurate, viable solutions — the technical bridge between customer impact and product teams.
Developed new processes and implemented improvements to eliminate gaps in support delivery.
Authored the original curriculum for a 3–5 week onboarding program covering new Support Engineers and other roles joining the team — later adopted by the broader training team as its standard framework. Continued delivering it quarterly to cohorts of up to 10 new engineers, while mentoring 3–5 engineers on an ongoing basis.
Created, refined, and updated 10–15 articles a month within a several-hundred-article internal knowledge base supporting close to 1,000 users globally — keeping information, screenshots, and processes accurate as products and workflows changed.
Established and maintained internal Azure test beds running IaaS and PaaS workloads for the support team — hands-on Azure infrastructure work running alongside the support role.

Senior Customer Support Engineer

2014 – 2020

Microsoft Corporation · Redmond, WA

Founding member of Microsoft's Azure Government support team from its inception through its transition into an independent reporting structure — a select team requiring a full federal background check to support customers on a completely siloed, access-controlled government cloud environment.
Managed Azure subscription, account, and billing issues for Microsoft's S500 enterprise customer base — including Verizon, NTT Technologies, CenturyLink, and Sony — minimizing production downtime and fiscal impact.
Troubleshot Azure environment outage events, providing professional paths to resolution under time pressure for enterprise SLAs.
Collaborated with SaaS, IaaS, and PaaS partner teams to uncover root causes for complex customer issues requiring cross-team coordination.

Hands-on Azure Projects

AI-103 project: Intelligent Insights Platform (in progress)

2026 – Present

Building an event-driven AI pipeline on Azure AI Foundry: Blob upload → Event Grid → Storage queue → Azure Functions (Flex Consumption) → a Foundry agent with tool calling. Deployed entirely with Bicep and run with no keys or secrets: managed identities throughout, and an Entra ID sign-in that uses a federated credential instead of a client secret — ostebovik.net/ai-foundry.
Root-caused a broken retry path: the permissions Microsoft documents as the queue trigger's minimum can't release a failed message back to the queue, so the configured retry delay never applied. Proved it with a targeted probe and a negative control, then replaced two broad built-in roles with one least-privilege custom role and re-tested the failure path on its own.
Designed an 18-entry least-privilege access model (who can reach what, at which scope, and why) and tested it against the live tenant; certified a multi-tool agent against a pre-registered acceptance test: 120 of 120 runs completed and measured, zero crashes, with every run traceable to its exact code version.

AZ-104 projects: 14 hands-on Azure labs

2025 – 2026

Deployed a full production Azure environment using Bicep IaC and GitHub Actions CI/CD — Front Door, Static Web App, Key Vault with Managed Identity and RBAC-scoped secret references — live at ostebovik.net.
Built Azure Monitor pipelines using Data Collection Rules and the Azure Monitor Agent, authoring KQL queries and configuring alert rules and action groups — documented lab work at ostebovik.net.
Implemented Azure Backup and Site Recovery configurations including Recovery Services Vault policies, MARS agent deployment, and ASR replication — translating direct customer exposure to backup failures into structured, documented lab coverage.

Earlier Experience

Senior Technical Support / Onboarding Engineer

2011 – 2014

Mercent Corporation · Seattle, WA

Built and maintained customized e-commerce integrations with XML, XSLT, XPath, and XQuery; resolved escalated issues requiring development-level changes and served as the bridge between support and development.

Founder & General Manager

2003 – 2010

Hot Yoga of Issaquah · Issaquah, WA

Acquired and turned around a failing small business, growing revenue 150%; managed finance, facility, and a staff of 10 instructors.

Developer Support Engineer

1999 – 2002

Onyx Software (Acquired by Consona Corp) · Bellevue, WA

Liaison between support and development on high-priority issues; created a self-service portal and knowledge base that reduced contact volume; QA-tested patches and trained support engineers.

Certifications

06 / 2026 AZ-104: Microsoft Certified Azure Administrator Associate Microsoft · 90A340-03CF69

02 / 2026 AZ-900: Microsoft Certified Azure Fundamentals Microsoft · 3547EB-50BR0E

10 / 2025 Certified in Cybersecurity (CC) ISC2 · 3093573