Chicago, IL · Open to Senior Leadership

Oksana Sobolevskaya

Engineering Leader · Platform & Cloud Architecture

I turn fragmented legacy environments into unified, high-availability platforms — aligning deep engineering rigor with business strategy, building teams of 30+, and delivering measurable impact at million-user scale.

20+

Years of
Experience

5M+

Devices
Supported

$1M+

Annual Savings
Delivered

30+

Engineers
Led

Get in Touch View Work

Oksana Sobolevskaya

Principal Engineering Consultant

Available for new opportunities

500K+

Log bundles processed daily
via Kafka / ELK

$500K

Annual SaaS fees eliminated
via modernization

6–10×

FTE-equivalent efficiency
gains recovered

Harvard

MS in IT · MIT ·
UCLA Anderson

About

Strategy meets
scaled delivery

With over 20 years of engineering leadership, I specialize in transforming complex, fragmented technical environments into cohesive, high-performing platforms that power millions of end users and deliver measurable business outcomes.

My career spans media, healthcare, public policy, and investment management — always at the intersection of deep engineering rigor and executive-level strategy. I've built and led cross-functional teams across the US, Ukraine, and Vietnam, delivering consistently under pressure and at scale.

"I don't just manage platforms — I architect the systems that allow organizations to move faster, spend smarter, and operate with confidence at any scale."

Based in Chicago, IL, I bring a global engineering mindset, deep AWS expertise, and a consistent track record of turning ambitious technical roadmaps into production-grade reality.

Education

Academic
foundation

Harvard University

MS — Information Technology

MIT

Quantum Computing Fundamentals

RUDN University

BS — Mathematics

UCLA Anderson

Technical Management Program

University of Chicago

Quantum Technologies

Experience

Work experience

Selected leadership roles and platform transformation work across complex engineering environments.

Principal Consultant

AdaITLink Inc. · Chicago, IL

Jun 2018 – Present

Platform Modernization Lead — AdResults Media

Defined target architecture for a Salesforce, NetSuite, and Redshift integrated campaign management system and led a multi-phase AWS cloud-native modernization.
Eliminated approximately $500K+ in annual SaaS fees by replacing a fragmented vendor stack with a unified event-driven platform.
Built and led a cross-functional team spanning backend, frontend, DevOps, QA, and business analysis, recovering 6–10 FTE-equivalent capacity and enabling more than $1M in annual operational gains.
Delivered Java and Python microservices on AWS with a React frontend, eliminating manual reconciliation across CRM, reporting, and data workflows.

Platform Engineering Lead — AT&T

Designed a distributed observability platform supporting 5M+ set-top boxes and reduced incident resolution from hours to minutes.
Built Kafka and ELK based systems processing more than 500K log bundles daily at billion-record scale.
Introduced AI-assisted diagnostics through LLM integration to automate log analysis and improve developer productivity.

Associate Director of Technology

DIRECTV / AT&T · Los Angeles, CA

Apr 2013 – May 2018

Led approximately 30 engineers across the US, Ukraine, and Vietnam, delivering high-availability backend platforms for millions of devices.
Owned Program Guide Web Services and Enterprise Guide Search, directing 10+ cross-team platform initiatives integrating dozens of internal and external data sources.
Designed Data Enrichment Services for scalable metadata ingestion via distributed processing across multiple external providers.
Introduced Jenkins CI/CD automation and strengthened incident response and root cause analysis.

Senior Engineering and Technical Leadership Roles

Media, healthcare, public policy, and investment management

2004 – 2013

Progressed through engineering leadership roles with increasing ownership across architecture, delivery, and platform modernization.
Led distributed systems implementation, backend services development, and enterprise integration efforts in complex operating environments.
Built the technical and organizational foundation for later executive-level platform and cloud leadership roles.

Skills

Core areas of expertise

A focused view of the leadership, platform, cloud, and delivery capabilities behind large-scale engineering transformation.

Engineering Leadership

Team Leadership 30+ System Architecture Platform Modernization Cross-Functional Leadership SDLC · Agile Roadmapping Production Reliability Global Teams

Cloud & Infrastructure

AWS (ECS · RDS · S3) Terraform Cognito · IAM · VPC EventBridge Docker Microservices CI/CD · Jenkins Ansible

Data & Platform Engineering

Kafka Elasticsearch / ELK OpenSearch · Lucene Hadoop · Redshift Data Pipelines Real-Time Processing Oracle · MySQL

Development & Tooling

Java / Spring Boot Python React REST APIs · SQL Git · Bitbucket Grafana · Splunk New Relic · Jira

AI & Emerging Tech

LLM Integration AI-Assisted Diagnostics Quantum Computing Event-Driven Architecture AI-Driven Automation

Strategy & Business

Technical Program Mgmt Stakeholder Alignment Change Management Cost Optimization Vendor Management Enterprise Architecture

Key Impact

Outcomes that
speak for themselves

$1M+

Annual Operational Efficiency Gains

Delivered by eliminating manual reconciliation and cross-system inconsistencies across CRM, reporting, and data workflows for a major media company.

AdResults Media · Cloud Modernization

$500K

Annual SaaS Cost Elimination

Transitioned a fragmented multi-vendor SaaS model to a unified, event-driven AWS platform — removing recurring license fees across Salesforce, NetSuite, and Redshift integrations.

AdResults Media · AWS Platform

5M+

Devices Supported by Observability Platform

Designed and delivered a distributed Kafka/ELK log analytics platform at AT&T, supporting millions of set-top boxes and cutting incident resolution from hours to minutes.

AT&T · Platform Engineering

6–10×

FTE-Equivalent Productivity Recovery

Automated previously manual workflows across a unified platform, freeing capacity equivalent to 6–10 full-time engineers and redirecting effort to high-value work.

AdResults Media · Automation

Let's Connect

Ready to build
something great

I'm actively exploring senior engineering leadership opportunities — VP, Director, CTO, or Principal roles — where I can drive meaningful platform transformation and build exceptional teams.