Jackie Grandison

Jackie Grandison is a Senior IT Systems Technician, AI Subject Matter Expert, and entrepreneur with over 20 years of experience at the intersection of enterprise technology, government operations, and human systems. Based in Montgomery, Alabama, she brings a rare combination of hands-on technical depth and forward-thinking strategy to every environment she serves.

In her current role as a Senior IT Systems Technician, Jackie serves as the primary IT point of contact for mission-critical government operations — managing enterprise infrastructure, endpoint support, network connectivity, instructional and emerging technology systems, Active Directory administration, and cross-agency system support. Her work routinely extends beyond standard business hours, a testament to her operational reliability and unwavering commitment to continuity.

Her professional journey began in the late 1990s and has traversed some of the most demanding technical and service environments in the region — from the U.S. Department of Education and Regions Financial Corporation, to Baptist Health's clinical systems environment, and ultimately to Alabama's state-level government infrastructure. She served as Lead Analyst for the Baptist Health Montgomery Cancer Center and played a key role in the Cerner FirstNet Go-Live at Baptist Medical Center East.

Jackie holds a degree in Computer Information Systems. Her certifications include CompTIA Security+, Network+, Cloud Essentials+, Project+, and ITIL Foundation, with advanced networking training completed through the CCNA Bootcamp. She is also an official member of ISC2, having earned the Certified in Cybersecurity (CC) credential — reflecting her continued investment in cybersecurity as a core discipline alongside her infrastructure and AI work.

In 2023, Jackie expanded into the world of Artificial Intelligence, joining Outlier as a Subject Matter Expert, where she contributes to the development and refinement of Large Language Models. This role sits at the convergence of her two greatest professional passions: disciplined systems mastery and the deployment of emerging technology.

A multi-award recipient recognized for Top Performance, Customer Service Excellence, Increased Initiative, and Conflict Resolution, Jackie does not collect accolades — she maintains a standard.

At the core of everything she does is one consistent commitment: bridging the gap between where systems are, and where they need to be — whether that system is an IT infrastructure, an organization, or a person.