Jesse Hembrook

16 years in Wisconsin state government: enterprise tax systems, testing, investigation, automation

Madison, Wisconsin area
jesse.d.hembrook@gmail.com  •  linkedin.com/in/jesse-hembrook  •  github.com/koorbmeh

16 yrs enterprise tax systems
Millions recovered in delinquent taxes
1 reversal in 14 yrs of legal determinations

— the only one

100,000+ employer accounts served

Profile

Business and systems analyst with 16 years inside Wisconsin's enterprise unemployment-insurance tax systems: requirements validation, user acceptance testing, defect documentation, and multi-source data investigation in a rules-driven compliance environment. Primary tester for two enterprise systems. One reversal in 14 years of issuing legally binding determinations. Recovered millions in delinquent taxes through data-driven investigation. Builds the automation as well as the requirements: desktop RPA (AutoHotkey v2) and AI-assisted workflow design, with verification and rollback designed in, backed by four Google AI credentials. Looking for an analyst seat where designing the faster, verified way is the job, not the workaround.

Core Skills

Automation & AI: Desktop RPA / Windows scripting (AutoHotkey v2) • Workflow design & process mapping • AI-assisted workflow design • Prompt engineering • Automation governance: verification and rollback

Data: SQL fundamentals • Relational database design & normalization • Data quality & auditing • Multi-source investigation • Mainframe systems (HOD, EXTRA)

Software Quality: User acceptance testing (UAT) • Test-case design & execution • Regression testing • Defect identification & documentation • Requirements gathering & validation • SDLC / waterfall implementation lifecycle • Java (OOP) • Primary tester, two enterprise systems

Domain: Wisconsin UI tax law (Ch. 108) • Compliance & appealable determinations • Financial reconciliation • Fraud detection

Experience

Wisconsin Department of Workforce Development, Madison, WI (Division of Unemployment Insurance, Bureau of Tax & Accounting)

Unemployment Tax & Accounting Specialist, Advanced

Feb 2021 – Present
  • Investigate and resolve the bureau's most complex employer tax cases; issue appealable legal determinations with a near-perfect record: one reversal in 14 years.
  • Research multi-source data across SUITES, UIBNET, and mainframe systems (HOD, EXTRA) to diagnose calculation errors, data-exchange failures, and file-submission problems.
  • Processed 100+ multiple-partial business transfers (complex COVID-relief cases); identified and documented a SUITES defect in reserve-fund-balance handling before it spread bad balances.
  • Propose system modifications and workflow redesigns; recurring source of process-improvement recommendations.

Unemployment Tax Collection Specialist (Entry → Senior)

May 2018 – Feb 2021
  • Recovered millions of dollars in delinquent unemployment-insurance taxes through account analysis, negotiated payment plans, and legal actions (liens, levies, garnishments).
  • Analyzed SUITES delinquency data to identify and prioritize collection targets; recommended statutory and procedural changes that improved collection efficiency.

Unemployment Tax & Accounting Specialist (Entry → Advanced)

May 2012 – May 2018
  • Primary tester for SUITES, the state's system of record for Wisconsin employer UI tax accounts: test-case development, user acceptance testing, rate testing, defect documentation, and requirements validation with developers.
  • Led the tester group for the bureau's Workflow system implementation; remained primary tester after go-live.
  • Served as UI data subject-matter expert on a DET/WEDC inter-agency data-sharing initiative: worked with partner agencies and DWD's IT Security Officer to define what data could be shared under what conditions, and surfaced the cost constraints that fed the decision not to proceed.
  • Identified a fictitious-employer fraud scheme and established the detection criteria adopted for ongoing screening.
  • Conducted independent-contractor and tax-liability investigations across trucking, logging, nonprofit, and fitness industries; promoted Entry → Advanced, noted in reviews for accuracy and rapid growth.

Employment Security Assistant 3

Jan 2010 – May 2012
  • High-volume confidential data processing across BMIS and NAC queues; reduced backlogs across multiple units while maintaining accuracy.

Independent Technical Projects

Automated knowledge & decision-support pipeline

Designed and run an unattended pipeline of scheduled jobs that screen inbound opportunities against a written rubric, advance open work items, and mine results into a versioned knowledge base, plus a weekly job that audits that knowledge base for its own errors. 500+ items screened unattended. Built the controls to match: backup before every write, byte-level write verification with automatic restore on failure, and single-writer locking, with every caught failure closing as a documented permanent control rather than a one-off patch.

Persistent AI memory architecture

Designed and operate a file-based memory system that gives AI agents continuity across sessions: index-first routing, capture and trust-tier rules, automated self-maintenance. Published the full architecture, with comparisons to vector-database and knowledge-graph approaches: markdown-brain.netlify.app

Interactive financial planning tools

Wrote and shipped a debt-payoff guide with an embedded client-side calculator and a dependency-free in-browser spreadsheet generator (vanilla JS producing valid .xlsx): bills-and-debt.netlify.app

VSQ: AutoHotkey v2 automation suite

Modular Windows desktop-automation suite (AHK v2) for a legacy gaming environment: event-driven scripting, reusable components, maintained long-term as a pinned public repo: github.com/koorbmeh

Education

Colorado Technical University, Coursework toward B.S. Information Technology

2012 – 2016

Software Application Programming specialization • 157 of 182 credits completed (86%) • GPA 3.92 • Dean's List • Completed coursework includes Software Requirements Engineering, Systems Analysis & Design, Project Management, Systems Acquisition, and Database Systems/SQL; all A's across the five-course Java sequence. Self-funded while working full-time; withdrew in good standing when funding was exhausted.

Certifications

Google: AI Essentials • Maximize Productivity With AI Tools • Use AI Responsibly • Discover the Art of Prompting (Oct 2025) • Atlassian Jira training paths completed (2026)

Mental Health First Aid (National Council for Mental Wellbeing, 2024) • FCC Amateur Radio Operator License (2022) • DWD Aspiring Leaders Training Series (2016)