AI & Automation Engineer

Jacob Monroe Johnson

I build intelligent systems that people actually use.

jacob.config
role: "AI & Automation Engineer"
background: ["tech", "finance", "people"]
superpower: "Bridging the gap between
  what AI can do and what
  people need it to do"
status: building|

Most AI engineers can build the system. Most advisors can manage the risk. I do both.

I started in the trenches — diagnosing DSL line faults at 2 AM, scripting network configs, bouncing line cards on Adtran systems. I earned a BBA in Computer Information Systems — a degree that fused technology with finance, accounting, economics, and quantitative methods — then spent 5+ years as a Risk Advisor, where I didn't just sell policies — I systemized risk management. I built Salesforce workflows, automated outreach funnels, trained teams on data integrity, and turned analytics dashboards into revenue machines.

Finance runs deep. I manage risk for families and businesses, run my own insurance practice at lainsurancequotes.com, and actively trade cryptocurrency using a custom framework rooted in market psychology, liquidity analysis, and capital allocation. Money management isn't a side skill — it's how I think.

Now I'm channeling all of it — the technical depth, the financial acumen, the people instincts — into AI and automation. I design multi-hop reasoning tasks that stress-test LLMs across 5–8 authoritative sources, engineer prompts that actually work at scale, evaluate model failures with surgical precision, and build automation workflows that eliminate the friction between humans and technology.

The market is flooded with people who can code AI. It's starving for people who can design the benchmarks, diagnose the failures, and translate it all for real humans in real businesses. That's me.

The Engineer

  • LLM Evaluation & Benchmarking
  • Multi-Hop Reasoning Task Design
  • Prompt Engineering at Scale
  • Conversational AI & Workflow Automation
  • Golden Trajectory Construction
  • SQL Scripting & Database Design
  • Network Architecture & Security
  • Systems Analysis & Diagnostics
×
📊

The Risk Advisor

  • Finance, Accounting & Economics
  • Risk Assessment & Management
  • Capital Allocation & Money Management
  • 33% YoY Revenue Growth
  • CRM Optimization (Salesforce)
  • Team Training & Enablement
  • Stakeholder Communication
  • Data-Driven Decision Making

AI & Evaluation

LLM Evaluation Multi-Hop Reasoning Design Prompt Engineering Golden Trajectory Authoring AI Workflow Automation Conversational AI Model Failure Analysis Benchmark Design

Data & Systems

SQL Database Design Salesforce CRM Architecture Data Analytics KPI Dashboards

Networking & Security

Cisco Routers/Switches Wireshark Nmap Kali Linux Proxmox DNS / DHCP Network Diagnostics

Finance & Risk

Risk Assessment & Advisory Financial Analysis Capital Allocation Money Management Market Psychology Process Optimization Marketing Automation Team Enablement
01
Government & Law Task Designer Evaluator

Municipal Records & Historical Reasoning Task

Designed a natural-language question requiring an LLM to combine historical, geographical, and municipal-record clues across 5+ authoritative sources to reach a single numeric answer. Tests multi-hop reasoning, temporal anchoring, entity disambiguation, and document-based extraction.

Final Answer 9,812 ft²

Reasoning Chain

1Identify festival → Burning Foot Beer Festival
2Identify beach & city → Pere Marquette Beach, Muskegon, MI
3Identify missionary → Jacques Marquette (1637–1675)
4Identify medieval charter → Magna Carta (June 15, 1215)
5Identify influenced document → U.S. Constitution (1787)
6First signer George Washington → match to Washington Ave
7Extract lot size from 06-15-2023 Muskegon Planning Commission → 9,812 ft²
8 Model Runs
2 Correct
6 Failed
75% Failure Rate

Failure Modes Identified

Incorrect festival ID Bad historical mapping Surname → avenue failure Lot size extraction miss
02
Finance & ML Task Designer Evaluator

Academic Research & ML Metric Extraction

Designed a cross-domain reasoning task requiring an LLM to traverse 8 distinct authoritative sources — spanning ancient history, geography, institutional affiliations, national identity, award recipients, journal metadata, and deep-learning model metrics — to extract a specific Testing MAE from a peer-reviewed PDF.

Final Answer 1537.14424

Reasoning Chain

1Last ancient Wonder → Great Pyramids of Giza → Greater Cairo
2Identify institute → Higher Institute of Qualitative Studies (Heliopolis)
3Identify university → Capital University (Helwan), Decree 70
4Largest democracy → India → Vikram Sarabhai (father of space program)
52016 Sarabhai Medal recipient → Kohei Arai
6Identify journal → IJACSA, Editor-in-Chief Kohei Arai
7Extract TABLE XIV (LSTM model) → Testing MAE
8Final extraction → 1537.14424
8 Model Runs
3 Correct
5 Failed
62.5% Failure Rate

Failure Modes Identified

Geographic inference error Wrong award recipient Journal metadata miss PDF table extraction failure

What These Projects Demonstrate

🔗5–8 distinct authoritative sources per task
🧠Multi-hop reasoning across unrelated domains
🎯Deterministic, single-answer outputs
🔬Robust failure analysis across model runs
🗺️Golden Trajectory construction
📄Precision extraction from official docs & academic PDFs

Risk Advisor

Allstate Insurance — Paul Mims Agency

Oct 2025 — Present Monroe, LA
  • Advising clients on risk management across life, health, property, and casualty portfolios — assessing exposures, recommending coverage strategies, and building long-term financial protection plans
  • Operating lainsurancequotes.com — a self-built insurance quoting platform serving Louisiana residents
  • Applying CRM optimization, data-driven analysis, and the consultative approach that drove 33% YoY growth in prior role

Strategic Market Analyst — Cryptocurrency

Self-Employed

Jun 2023 — Present Remote
  • Built a custom analytical framework to streamline decision-making and reduce cognitive bias — the same systems-thinking that drives effective AI workflow design
  • Synthesized on-chain metrics, sentiment data, and macroeconomic signals to anticipate market shifts, achieving 15–20% monthly ROI
  • Applied rigorous risk management: stop-loss logic, capital allocation models, and portfolio balancing — maintaining <10% drawdown across cycles
How this builds AI skills →

Pattern recognition, data pipeline thinking, and building decision systems under uncertainty — core competencies for designing AI automation workflows.

Risk Advisor

Kim Duke State Farm

Aug 2019 — Jun 2023 West Monroe, LA
  • Drove 33% year-over-year sales growth through tailored recommendations and trust-based relationships
  • Trained team members on Salesforce optimization — lead prioritization, opportunity tracking, data integrity — producing a 20% team-wide productivity lift
  • Maintained 80%+ Drive Safe & Save setup rate, boosting auto policy retention by 12%
  • Engineered partnerships with lead providers (QuoteWizard, ZipQuote, HomeTown Quotes), increasing qualified lead flow by 20%
How this builds AI skills →

CRM architecture, workflow automation, team training on technical tools, and data-driven funnel optimization — all directly transferable to AI system deployment and user adoption.

Caretaker

Family Care

Jun 2017 — Aug 2019 Monroe, LA

Full-time care for elderly family member. Demonstrated empathy, adaptability, and problem-solving under pressure — the human-centered instincts that inform how I design technology for real people.

Marketing Coordinator

Kim Duke State Farm

Jan 2013 — Jan 2016 Monroe, LA
  • Generated 50+ qualified leads/month through 100+ daily outbound calls and consultative conversations
  • Configured Prospector+ automation — market segmentation, performance dashboards, bonus structures — streamlining operations
  • Built multi-touch drip campaigns, targeted lead lists, and digital marketing materials via Agent Advertise System
  • Managed paid ad campaigns across Facebook, Instagram, LinkedIn — delivering consistent 20%+ ROI
  • Synthesized analytics across Prospector+, Agent Analytics, and Control-D to equip leadership with actionable strategic insights
How this builds AI skills →

Marketing automation, analytics platform integration, and translating data into strategy — the exact workflow AI automation engineers optimize.

Level 3 Internet Support Specialist

CenturyLink

Oct 2006 — Nov 2011 Monroe, LA
  • Diagnosed DSL connectivity issues via Adtran systems — bouncing line cards, adjusting SNR margins, validating port configurations
  • Managed DNS infrastructure (A, PTR, NS records) through Network Solutions, ensuring accurate propagation
  • Resolved IP conflicts by accessing DHCP servers, releasing/renewing modem leases, and monitoring live negotiations
  • Executed system-level diagnostics to identify network anomalies and prevent latency or routing failures
  • Translated complex technical issues into jargon-free guidance — drastically improving resolution times and client satisfaction

Network Support Specialist

Bayou Internet

Jun 2005 — Oct 2006 Monroe, LA
  • Resolved network issues across DSL, VoIP, IPTV, and email services for end-users and field technicians
  • Diagnosed hardware/software conflicts impacting connectivity and service availability
  • Supported wireless infrastructure deployment — access points and mesh nodes — enhancing coverage and reliability
🎓

BBA, Computer Information Systems

University of Louisiana at Monroe

2011 — 2016

Hybrid foundation: finance, accounting, economics, marketing, statistics, systems analysis, database development, network design, network security, and project management.

🛡️

Information Technology

Applied Technology Center

2003 — 2005

Hands-on technical training in IT fundamentals, networking, and system administration.

📜

Producer License, Individual

Insurance Certification · License #LA-867875

Licensed across life, health, property, and casualty lines.