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Jason Helrigle

@jasonh

Director of IT & technology leader delivering enterprise infrastructure strategy and AI-powered automation for measurable business outcomes.

United States

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What I'm looking for

I’m seeking a Director of IT, VP of Technology, or Head of Technology role at a growing organization where I can own the full technology function, build and lead the right team, and drive measurable business outcomes through technology investments.

I’m a senior technology leader with 20+ years of progressive experience across software engineering, enterprise infrastructure architecture, and AI-powered automation. My career spans production financial applications at Wells Fargo, Fortune 500 infrastructure leadership at Dell Technologies, and architecture strategy direction for mid-enterprise clients across hybrid cloud, virtualization, and data protection.

As an Advisory Solutions Architect and Senior Solutions Architect, I owned complex engagement lifecycles—from business discovery through architecture design and executive presentation—translating requirements into implementable strategies. I directed multi-vendor solutions (Dell, VMware, AWS, Azure), managed vendor/partner relationships at scale, and produced executive-level deliverables including architecture diagrams, implementation roadmaps, and ROI/TCO analyses.

Today, as a Self-Employed Technology Consultant & AI Engineer, I design and deploy intelligent automation systems, lead technology strategy engagements, and build full-stack web applications. I bring deep hands-on engineering strength with enterprise governance, security/compliance mindset, and a clear focus on building and leading the right team to deliver measurable business outcomes.

Experience

Work history, roles, and key accomplishments

Current

Technology Consultant & AI Engineer

Current

Self-Employed

Jun 2025 - Present (9 months)

Delivered AI-powered automation, technology strategy advisory, and application development for small and mid-market organizations. Designed multi-agent automation for document processing, customer service routing, content generation, and reporting with human-in-the-loop governance, and built full-stack web applications using Python, FastAPI, React/Next.js, and Supabase including SaaS billing integ

Intelligent Automation Document Processing Python fastAPI Next.js Supabase SaaS Integration Human In The Loop technology strategy

Advisory Solutions Architect

Level Solutions Group

Mar 2021 - May 2025 (4 years 2 months)

Served as a senior technical authority for complex infrastructure engagements, owning the full lifecycle from discovery through executive presentation for organizations supporting 500–5,000 users. Led hybrid cloud and security-focused requirements analysis, designed multi-vendor solutions across Dell, VMware, AWS, and Azure, and produced ROI/TCO and implementation roadmaps that guided technology i

Enterprise Architecture VMWare AWS Azure Network Security Vendor Management Requirements Analysis

Senior System Engineer

Dell Technologies

Nov 2010 - Sep 2020 (9 years 10 months)

Provided technical leadership for enterprise infrastructure engagements across storage, compute, converged/HCI, data protection, and networking. Built reference architectures and requirements/validation analysis, and created ROI/TCO business cases presented to C-level and senior executives.

Enterprise Infrastructure Data Protection VMWare

Software Engineer, Business Systems

Wells Fargo

Oct 2003 - Nov 2010 (7 years 1 month)

Built and maintained enterprise software solutions in a regulated, high-availability environment with reliability and business continuity as non-negotiable requirements. Developed a tier-1 fraud detection application delivering daily analytical reports, led a two-year enterprise upgrade coordinating requirements and releases, and automated complex workflows to replace manual processes across busin