Casey Shingledecker — professional headshot
Technology Support · AI Systems · Cybersecurity-Bound · Minnesota

Casey Shingledecker

I build and operate multi-agent AI systems, keep technology working for the people who depend on it, and I'm documenting a deliberate move into cybersecurity — in public, including the parts that don't go smoothly, because troubleshooting is the job.

Tier 1/2 IT SupportGoogle Workspace · Microsoft 365MCP · Multi-Agent OrchestrationCompTIA A+ in progressCybersecurity bootcamp · 80%

AI Systems & Automation

Self-directed engineering projects — designed, built, tested, and independently verified.

FLAGSHIPMulti-Agent OrchestrationModel Context Protocol (MCP)Claude · Gemini · Grok · Hermes

The Tree — Hierarchical Multi-Agent Orchestration System

Problem. A single AI agent asked to deliver a whole project skips steps, grades its own homework, and fails silently. Production-quality delivery needs planning, approval gates, execution, and verification by separate parties — the same separation of duties a real engineering organization uses.

Architecture. A three-level agent hierarchy — one Grand Strategist (orchestrator), three domain Advisors (architecture / implementation / verification), and tiered execution sub-agents routed by cost-of-being-wrong across frontier and efficiency-class LLMs. Nine governing laws: chain of command, plan-before-action with explicit approval gates, independent verification, halt-don't-guess escalation, two-strike tier escalation, step budgets, and a files-are-truth audit trail. Built on Model Context Protocol (MCP) with structured JSON-schema tool calling; every mutation is git-checkpointed. Packaged as a reusable skill with exportable prompt packs for Claude Desktop and the Hermes agent ecosystem.

Implementation. Deployed as a production skill and validated on an end-to-end calibration build: 11 gated tasks, every one through plan → advisor approval → gated execution → independent audit, with a complete on-disk paper trail (plans, approvals, verdicts, results, flight log).

Key results (verified).

2specification defects caught by the audit gate before any code existed
248/248tests passing, re-verified in an independent clean-room run
13/13graded acceptance checks passed across both trial missions
14coordinated agents; zero escalation failures, zero retries burned
LIVE DEMODashboard UILocal AI runtimes

Kanto Command — AI Operations Dashboard

Problem. A local multi-agent ecosystem (Hermes) — formerly Hermy Command Center — had no single pane of glass — agent states, execution traces, task queues, and runtime telemetry lived in scattered terminals, so a stalled agent could burn compute unnoticed.

Build. A centralized mission-control interface — agent roster and hierarchy view, live activity feed, approval inbox for gated actions, task tracking, and inference telemetry — engineered as one self-contained HTML/CSS/JavaScript application (~100 KB, zero dependencies). Supervises local model runtimes (Ollama, LM Studio), balancing latency, privacy, and compute cost. Dark-first UI with a custom pixel design system.

▶ Open the working interface — this is the actual dashboard, not a mockup.

Case studyPythonpytestSpec-first

pwstrength — built by The Tree

To prove the orchestration system on real work, The Tree built a password-strength analyzer end-to-end: three sealed spec documents, a scoring library (five criteria: length, character variety, uniqueness, common-password matching, repetition/sequence penalties), a CLI, and a 248-test suite.

Why does "password" score 0/100? It takes the maximum dictionary penalty, has one character class, and gains too few length points to recover — exactly what the published scoring spec predicts. Clean exit codes (0 success · 2 usage error), deterministic output proven across processes.

The audit gate failed the specs on the first pass — two real defects, fixed and re-verified before implementation began. That failure is the system working.

In progressAI ecosystemKnowledge management

Personal AI Ecosystem — shared memory across agents

Current build: a synchronized knowledge fabric (Obsidian Sync vault) shared by Claude Desktop, a Hermes cloud agent (Nous Portal), a local Hermes agent, and the Command Center — so every agent reads the same project files, decisions, and memories. Model routing by cost-of-being-wrong: a frontier orchestrator, an independent advisor model, and efficiency-class sub-agents. Documented as it's built.

Cybersecurity Journey

A deliberate, documented pivot — labs in public, credentials in sequence, employer-sponsored.

Bootcamp & labs

  • Chegg Skills Cybersecurity Bootcamp (Network Administrator & Cybersecurity Analyst track) — 80% complete, expected September 2026, sponsored through Target's employer education benefit.
  • 33+ hands-on labs: pfSense firewall hardening, OpenVPN, WEP/WPA traffic analysis, disk encryption, hash validation, Active Directory, RADIUS, vulnerability scanning, web-application exploitation, Linux log analysis with grep/gawk.
  • Course 1 capstone complete-track, including malicious-indicator analysis and the Target breach case study.
  • Lab writeups published at cybersecurity-journey-labs — each one a real problem, a documented method, a verified result.

Certification path — CompTIA trifecta

A+ Core 1 (220-1201)● IN PROGRESS
A+ Core 2 (220-1202)○ QUEUED
Network+ (N10-009)○ QUEUED
Security+ (SY0-701)○ QUEUED

Sequenced deliberately: Security+ assumes networking fluency it doesn't teach — I'd rather hold the credential and the competence at the same time.

Core Competencies

Organized the way recruiters and applicant-tracking systems actually read.

AI & AUTOMATION

  • Model Context Protocol (MCP)
  • Multi-agent orchestration
  • Autonomous agent design
  • Prompt & system-prompt engineering
  • Claude · Gemini · Grok · Hermes
  • Ollama · LM Studio (local inference)
  • LLM API integration
  • Structured / JSON-schema tool calling
  • Agent memory & knowledge management (Obsidian)

SYSTEMS & IT SUPPORT

  • Tier 1/2 help desk & troubleshooting
  • Google Workspace administration
  • Microsoft 365 administration
  • Windows 10/11 device support
  • Device configuration & imaging
  • Account provisioning · IAM fundamentals
  • Hardware repair & workstation integrity
  • Systems documentation & runbooks

SECURITY & NETWORKING

  • pfSense firewall hardening
  • OpenVPN · RADIUS · Active Directory
  • Vulnerability scanning & assessment
  • Disk encryption · hash validation
  • Linux log analysis (grep / gawk)
  • TCP/IP · DNS · DHCP fundamentals
  • Physical security controls
  • Incident & indicator analysis

DATA & QUALITY

  • Data integrity QA
  • Public-records & background research
  • Court & government database research
  • Discrepancy auditing
  • Compliance tracking & logging
  • Investigative report writing

OPERATIONS & LEADERSHIP

  • Team leadership, training & coaching
  • Building-systems monitoring
  • Preventive maintenance
  • Regulatory compliance (CPO)
  • Inventory & fulfillment systems
  • Event & testing logistics

COMMUNICATION

  • Technical documentation
  • End-user training
  • Customer & guest technology consultation
  • Cross-cultural & bilingual communication
  • Instructional design
  • Cross-functional coordination

Experience

Eighteen years of making complex things work — international education, records research, K-12 technology support, facilities operations, and consumer technology.

CURRENT

Tech & Electronics Team Member — Target

Oct 2025 – Present · Tech & Electronics since Sept 2026 · Fulfillment & Logistics Oct 2025 – Aug 2026
  • Consult guests on consumer technology — devices, connectivity, smart-home, and accessories — diagnosing needs, troubleshooting compatibility questions, and configuring the right solution at the point of sale.
  • Maintain electronics-department inventory accuracy and merchandising standards using handheld inventory systems for counts, locates, and replenishment.
  • Executed digital-order fulfillment (Order Pickup, Drive Up, ship-from-store) against accuracy and time-to-fulfill targets using handheld inventory and pick-path systems (Oct 2025 – Aug 2026).
  • Enrolled in the Chegg Skills Cybersecurity Bootcamp through Target's employer-sponsored education benefit — 80% complete, on track for September 2026.

Night Custodian Lead (Facilities Operations) — Blackhawk Middle School, Independent School District 196

Oct 2024 – Oct 2025
Eagan, MN
  • Led night facilities operations for a middle-school campus — built the night crew from the ground up and directed it through targeted training and performance coaching.
  • Monitored and maintained building systems (boiler monitoring, minor plumbing, electrical troubleshooting) and enforced physical security controls — door-locking protocols and lighting management — across the campus.
  • Operated the school swimming pool to state health code with daily water-chemistry testing and logging (pH, chlorine, alkalinity); earned the Certified Pool & Spa Operator (CPO) license, February 2025.
  • Managed event setup/teardown logistics and campus-wide cleaning, sanitation, and floor-care programs to keep facilities ready for immediate reuse.

Technology Support Specialist — Washburn Elementary, District 271 Public Schools

Sept 2023 – Aug 2024
Bloomington, MN
  • Resolved Tier 1/2 hardware, software, and account issues across Google Workspace for Education and Microsoft 365, maintaining classroom continuity under strict district compliance standards.
  • Served as the school's sole standardized-testing coordinator, administrator, and proctor — provisioning student accounts, configuring secure testing devices, and maintaining workstation integrity through every testing window.
  • Administered student accounts and records alongside technical troubleshooting; documented resolutions into reusable procedures for staff.

Role concluded when Washburn Elementary closed under district budget constraints.

District-Wide Custodial Float — Independent School District 196

Sept 2020 – Sept 2023
Apple Valley, MN
  • Rotated nightly across district buildings, restoring classrooms, hallways, and common areas to standard — deep floor care, surface disinfection, lighting and temperature control — so every site opened ready for students and staff.
  • Adapted to a different building, team, and priority list each shift through the pandemic era; a three-year record of reliability that led directly into the District 271 technology-support role.

Research Specialist — Omni Data Retrieval

Aug 2018 – Sept 2020
Lakeville, MN
  • Conducted rigorous, multi-layered background investigations across U.S. court records, government databases, and private-sector systems, sustaining audit accuracy above 99% in an environment where a single error could cost someone employment or a security clearance.
  • Produced investigative reports engineered to withstand stringent scrutiny — unambiguous conclusions backed by verifiable evidence.
  • Standardized documentation and query-verification procedures to protect data integrity and minimize compliance risk.

Professional English Tutor & Cross-Cultural Communications Specialist — Independent Practice

Dec 2007 – May 2018
Tokyo, Japan
  • Built a freelance English-instruction business from a single English-café contract into a practice supporting 70+ teaching hours per week across multiple locations, through strategic marketing and word-of-mouth referrals.
  • Designed and delivered immersive curricula to learners from early childhood (St. Francis Private Catholic School, Kameari) through corporate executives, adapting instruction across ages, goals, and backgrounds.
  • TEFL International 120-hour TESOL certification (2013). Returned to the U.S. in 2018 to begin the family visa process.

Education & Credentials

Formal coursework, professional certifications, and current programs.

Chegg Skills — Cybersecurity Bootcamp

Network Administrator & Cybersecurity Analyst track · Remote · 80% complete · expected Sept 2026

Employer-sponsored (Target). 33+ hands-on labs across firewalls, VPN, directory services, encryption, vulnerability assessment, and log analysis.

CompTIA Certification Path

A+ Core 1 (220-1201) in progress → A+ Core 2 → Network+ (N10-009) → Security+ (SY0-701)

Sequenced so the networking foundation is in place before the security credential.

Certified Pool & Spa Operator (CPO)

Pool & Hot Tub Alliance · Plymouth, MN · License C-121031 · Feb 2025

Regulated-facility operations: water-chemistry testing, compliance logging, and public-health code adherence.

TEFL International — 120-Hour TESOL Certification

Awarded Feb 2013

Teaching English to Speakers of Other Languages; foundation for a decade of instructional design and end-user training.

Full Sail University

B.S. Web Design & Development program (online) · Winter Park, FL · 2010 – 2012 · 50 semester credits

Coursework: Networks & Server Structures · Human-Computer Interaction & Usability · Web Standards Design · Designing & Advanced Computer Graphics · Intellectual Property & Law · Principles of Production Process.

Dakota County Technical College

Rosemount, MN · Fall 2023

Microsoft Word & Microsoft Excel certification coursework (ADMS 1260 / ADMS 1265).

Creative Engineering

A decade of self-taught game development, animation, design, and audiovisual production — the systems-thinking foundation under the AI work.

Contact

Open to technical operations, IT support / help desk, AI systems support, and security-track roles — Minnesota (Twin Cities) or remote.