Martin Gleason

I am a justice-system operator who builds and deploys AI — and for 26 years I have been the government agency an AI strategist advises.

As Deputy Chief Probation

Officer at Cook County Juvenile Court and Probation Services, I direct the department's training and professional-development function and put Anthropic's Claude into production for compliance and analytics tooling under real county IT constraints. I have produced the deliverables this role describes from the agency side: a data-driven strategy that brought all 217 sworn officers into statutory compliance, a capital investment case that cleared a chief judge's budget and finance review, and a practice framework briefed to the juvenile court bench and presented nationally. I know what a practical AI roadmap has to survive inside a public agency, because I am the person it lands on.

Deputy Chief Probation Officer — Training & Professional Development at Cook County Juvenile Court and Probation Services (2024-11 – Present)

Direct the department's training and professional-development function, accountable for the statutory training compliance of 217 sworn probation officers; manage five supervising probation officers across concurrent program lines.

• Build and deploy AI-assisted training and compliance tools with Anthropic's Claude in production — including the COPE processor, a web app now in testing that turns staff spreadsheets into a state-mandated presumptive-provider log — inside the security, procurement, and data-governance constraints of a county justice agency.
• Authored and shepherded a capital investment request for an enterprise project-management platform through the Office of the Chief Judge's budget and finance review: scoped licensing and implementation services, built the ROI case, and addressed legal and data-governance considerations across a multi-stakeholder government buying cycle.
• Built the Social Determinants of Probation protocol, a seven-domain assessment framework adapted from the social determinants of health; briefed it to the Cook County juvenile court judges and presented it at the American Probation and Parole Association's 2025 national conference.
• Designed the data-driven strategy that brought all sworn staff into compliance with Administrative Office of the Illinois Courts statutory training mandates, using data to identify gaps and target required trainings.
• Redesigned the new-hire legal evaluation into four sequenced, adult-learning-based assessments — steering executive leadership past the objection that the old test was the "only objective measure" of new-hire fit — achieving a 100% pass rate across 32 new hires in FY 2025–2026.
• Conducted a workload analysis of the department's performance coaches and converted the findings into sustainable, data-based caseload standards; created the KPIs that measure the Office of Career Services' effectiveness.

Supervising Probation Officer — Case Management System Administration at Cook County Juvenile Court and Probation Services (2022-01 – 2024-11)

Served as the department's first case management system administrator, leading the unit responsible for the enterprise system of record for legally protected juvenile information.

• Acted as the bridge between a commercial software vendor and a large county agency: gathered requirements from policy, technical, and end-user stakeholders, scoped and prioritized new system capabilities, and translated findings into concrete vendor deliverables.
• Wrote the policy and protocol governing how staff enter case notes, contacts, and referrals — the department's data-entry, records-management, and data-integrity standards, written in plain language for line staff rather than IT.
• Developed structured testing plans and acceptance evaluations that surfaced defects and regressions early, interpreting results and driving vendor fixes and interim mitigations while protecting operational continuity.
• Redesigned geographic service boundaries using ArcGIS and R, increasing pre-trial services capacity by 25%; authored documentation that cut new-user onboarding time by 50%.

Probation Officer / Trainer, Office of Career Services at Cook County Juvenile Court and Probation Services (2017-10 – 2022-01)

• Led the testing, training, and deployment plans that launched a new enterprise case management system during 100% remote operations, on an unmovable timeline.
• Built a zero-to-one web-based data collection and reporting system that raised statutory training-hour compliance to 100% and cut AOIC reporting time by 50%.
• Created data-science fundamentals training that made technical and analytical concepts accessible to non-technical court staff; designed the onboarding program for 10 new probation officers.
• Taught myself Python to build and demo a proof-of-concept geocoding API for automated courtroom case assignment on probation-issued equipment; presented at GIS Day 2020.

Probation Officer / Juvenile Advisory Council Facilitator at Cook County Juvenile Court and Probation Services (2012-12 – 2017-10)

Led a standing team of youth consultants — the nation's first court program incorporating youth perspective into juvenile court operations — recruiting, training, and directing justice-involved young people to advise the court on its programming and practice, in consultation with the Annie E. Casey Foundation.

• Diagnosed through an R root-cause analysis why 33% of program invitations never reached families, implemented the fix, and increased attendance by 50%.

Probation Officer and Treatment Specialist at Cook County Juvenile Court and Probation Services (2000-06 – 2012-12)

Master of Science in Information Systems – DePaul University

Bachelor of Arts in Psychology and History – Beloit College