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Raymond Bankoski

@raymondbankoski

Technology executive and AI automation strategist driving digital transformation and scalable enterprise modernization.

United States
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What I'm looking for

I’m looking for an executive leadership role where I can drive AI-assisted automation and digital transformation, partner with executive teams, and modernize enterprise cloud, data, and integration to deliver measurable operational impact.

I’m a technology executive who leads enterprise modernization, AI adoption, workflow automation, and cloud/infrastructure strategy, with a track record of aligning technology choices to business outcomes. In my current role as Chief Technology Officer, I drive digital transformation across software engineering, automation, compliance, and enterprise communications for a multi-state organization.

I architect AI-assisted document processing and intelligent workflow automation to reduce manual effort, improve compliance, and accelerate throughput. I also design and implement enterprise automation platforms integrating SQL Server, Azure services, APIs, RPA technologies, and custom .NET applications—so teams can scale operational execution with confidence.

Previously, as Vice President of Content and Metadata and later Vice President of Electronic Asset Management, I led global digital operations teams and replaced legacy workflows with automated, software-driven systems. I delivered measurable results, including improving efficiency by more than 80% versus manual processing and reducing manual labor by more than 50% with Robotic Process Automation (UiPath), while directing Lean Six Sigma initiatives and mentoring cross-functional, distributed teams.

Experience

Work history, roles, and key accomplishments

SP
Current

Chief Technology Officer

Stenger & Stenger, P.C.

Jan 2021 - Present (5 years 5 months)

Architected AI-assisted document processing and intelligent workflow automation to reduce manual processing, improve compliance, and accelerate operational throughput. Designed enterprise automation platforms integrating SQL Server, Azure services, APIs, RPA, and custom .NET applications, leading modernization across security, identity management, and enterprise systems integration.

GL

Vice President, Content Metadata

Gale, Cengage Learning

Jan 2006 - Jan 2021 (15 years)

Led global technology, metadata, and digital operations teams for enterprise content processing, metadata engineering, and workflow automation. Implemented automation that improved operational efficiency by 80% versus manual processing, deployed UiPath RPA to reduce manual labor by 50%, and managed distributed and offshore teams.

GL

Vice President, Electronic Asset

Gale, Cengage Learning

Jan 1997 - Jan 2006 (9 years)

Managed enterprise image capture, metadata architecture, OCR workflows, and digital publishing systems supporting Gale Digital Archives. Played a key role in the operational design of a $100M+ digital publishing product line containing 250M+ data objects and led launches with globally distributed and offshore teams.

Education

Degrees, certifications, and relevant coursework

Southern Connecticut State University logoSU

Southern Connecticut State University

Bachelor of Science, Computer Science

Activities and societies: Trained as a Six Sigma Black Belt.

Earned a Bachelor of Science in Computer Science from Southern Connecticut State University.

Tech stack

Software and tools used professionally

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