Open to VP of IT, CIO & fractional roles
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Shawn Gifford

Vice President, Information Systems / Fractional CIO
Illustration of Shawn Gifford leading an agentic automation design session in a boardroom

Technology exists to unlock human potential — not the other way around. I walk into organizations where IT has been treated as a cost center and change the equation: through patient listening that turns skeptical executives into strong allies 8 times out of 9, and early wins that have driven 62% average process efficiency improvements. The result isn't just better technology — it's IT as a strategic partner, not in title but in practice.

62%
Avg. process efficiency gain across CoE deployments
8 of 9
Skeptical execs turned into strong allies
11 hrs
DR recovery vs. 48-hour target (HQ outage)
About

Shawn is a technology executive with 26 years in IT — the last 11 in senior leadership — most recently as CIO / VP of Information Systems at The Baby Fold, reporting directly to the CEO and board. His path into the C-suite is unusual: engineering mechanics and psychology research at the University of Illinois, a summer inside a Department of Energy facility designing non-nuclear components for the U.S. nuclear stockpile, and fifteen years as a hands-on infrastructure engineer, vCIO, and fractional IT manager before ever taking a full-time management title.

That path is also the point. Deep technical depth, executive fluency, and a psychology-trained instinct for what people actually need from technology — combined, they make him hard to categorize and effective in the seat. Across four employers he has repeated the same pattern: take an under-resourced or under-governed IT organization and rebuild it into a strategic asset. Modern cloud infrastructure. Real data governance. Board-approved AI adoption that gets used, safely. Automation Centers of Excellence that outlast his own tenure.

He's now exploring his next VP or CIO seat — and taking on select fractional and interim engagements for organizations that need executive IT leadership without a full-time hire.

Career Journey

Four employers. The same pattern. Better every time.

From hands-on sysadmin serving Fortune 500 clients to the CIO seat at a 120-year-old nonprofit — a two-decade arc where the technical scope grew but the philosophy stayed the same.

2000 — 2004
PTC Select
Systems Administrator / Consultant
Built the technical foundation. Clients included Caterpillar, State Farm, and Komatsu. MCSE, CCNA, CompTIA — the credentials that substituted for a degree he'd left behind.
2004 — 2014
Heart Technologies
IT Manager / vCIO
Rose from senior tech to department lead while carrying ~40 billable vCIO hours weekly. Spotted Hyper-V early, drove Heart to Microsoft Gold Partner status. First convergence of psychology and IT.
2015 — 2023
Illinois Mutual
IT Infrastructure Manager
Team of 14, $13M budget. Founded the Automation CoE (still running today). Led DevOps→DevSecOps transformation. Led the response when HQ went dark at 11:30pm on a Friday.
2023 — 2026
The Baby Fold
CIO / VP, Information Systems
Reporting to CEO, on the Executive Leadership Team. Three-year strategic plan at 95% completion. Board-approved AI policy. In-house Service Center. Second CoE — this one, agentic AI from day one.
Signature Work

Three moves that defined the seat.

Infrastructure
12x / 10x
Datacenter to Cloud, twice.
Delivered the same signature outcome at both Illinois Mutual and The Baby Fold — 12x compute and storage capacity paired with a 10x (~90%) reduction in physical footprint — migrating legacy systems to AWS and Azure and replacing them with modern SaaS platforms.
AI Governance
Consent Agenda
First board-approved AI policy.
Walked into ungoverned AI sprawl with real HIPAA and DCFS exposure. Built the policy from scratch with the COO, Clinical Director, and VP of QI. Navigated open executive opposition. It passed the board on consent agenda — without a single question — and became the launchpad for the agency's first agentic deployments.
Automation
6 wins · 60% avg
Two Centers of Excellence, built to outlast me.
Founded Illinois Mutual's first Automation CoE — six RPA deployments averaging 60% efficiency gains, still operating after my departure. At The Baby Fold, built a second CoE that skipped RPA entirely and went straight to agentic AI, delivering DCFS file automation and a clinical outcomes agent.
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Let's Talk

Hiring a VP of IT or CIO — or need fractional coverage while you look?

Whether it's a full-time seat or a fractional engagement to stabilize IT during a transition, I'm glad to talk through where you are and where you need to get to.

This page was designed and built in collaboration with Claude — layout, copy, and a working AI chatbot trained on Shawn's full career history — as a demonstration of how he puts agentic tools to work.