AI Evaluation Engineer

Jacob Monroe Johnson

I design the benchmarks that make AI models smarter.

jacob.config
role: "AI Evaluation Engineer"
background: ["tech", "finance", "people"]
superpower: "Designing the scenarios
  that break AI models —
  then teaching them to win"
status: building|

Most AI engineers can build the system. Most annotators can label the data. I engineer the scenarios that teach models how to think.

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, engineered lainsurancequotes.com as a digital brand to capture and qualify local lead traffic, 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 evaluation and training data engineering. I design complex agentic tool-use scenarios and web-source reasoning tasks that generate RLHF/SFT training data for large language models. I work backwards from deterministic answers to construct multi-hop reasoning chains, author golden trajectories with atomic fact verification, build rubrics, and analyze model failures with surgical precision — all through rigorous QA pipelines with 10–15+ validation checkpoints per task.

The market is flooded with people who can use AI. It's starving for people who can design the benchmarks, engineer the training data, and diagnose the failures that make models actually improve. That's me.

The Engineer

  • RLHF/SFT Training Data Design
  • Golden Trajectory Authoring
  • Multi-Hop Reasoning Task Design
  • Agentic Tool-Use Scenario Design
  • Model Failure Analysis & Rubrics
  • Atomic Fact Verification (Fan-Out)
  • Prompt Engineering at Scale
  • Systems Analysis & Diagnostics
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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

RLHF/SFT Data Engineering Golden Trajectory Authoring Multi-Hop Reasoning Design Agentic Tool-Use Design Model Failure Analysis Rubric & Benchmark Design Atomic Fact Verification Prompt Engineering

Data & Systems

SQL & Relational DBs Salesforce CRM Architecture n8n & Workflow Automation Flowise & LLM Orchestration Synthetic Data Pipelines API & JSON Schema Design Data Analytics & Reporting KPI Performance Dashboards

Networking & Security

Cisco Infrastructure Routing Proxmox & LXC Virtualization Wireshark Packet Analysis Nmap Network Scanning Kali Linux Security Auditing OPNsense & Nginx Proxy DNS / DHCP Protocols System & Network Diagnostics

Finance & Risk

Risk Assessment & Advisory Financial & Portfolio Analysis Capital & Resource Allocation Money & Risk Management Market Psychology Process & Funnel Optimization Marketing Automation Team Enablement & Training
01
Telecom & ISP Task Engineer

Agentic Tool-Use Evaluation (Bayou Dental Scenario)

Designed a highly complex, 6-tool agentic workflow to test an LLM's cross-tool entity matching and temporal reasoning. Engineered a synthetic, noise-heavy environment (800+ objects, 300+ arrays) requiring the model to filter decoys and track state across systems.

Agentic Tool Flow

Media Control Contacts Jira Calendar Messages Gmail

Developer Instructions (Failure Triggers)

Utilized a 2-run methodology: Run 1 passes cleanly. Run 2 introduces strict developer instructions to force measurable, attributable failure.

Constraint: "All mobile messages must be ≤25 words, single sentence"
Constraint: "Execute tool calls one at a time, no parallel batching"
Constraint: "Before modifying any Jira issue, read it first by ID"

Failure Modes Identified

Entity disambiguation (similar tech names) Temporal reasoning failure Verbose output violation State tracking failure
02
Government & Law Task Engineer

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
03
Finance & ML Task Engineer

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
04
Film & Media Video Annotator

Multimodal Video Evaluation — Project Voyager (Handshake AI)

Authored rubric-based prompts against video clips engineered to stump LLMs through precise audio-visual integration. Each prompt required genuine multimodal reasoning — answers could not be confirmed from audio or video alone — bounded by a 1–2 minute context window defined by two observable events.

Prompt Design Constraints (3 Golden Rules)

1Unambiguous — scoped to a specific two-event time window; any two viewers interpret it identically
2Verifiable — each rubric criterion independently confirmable from the clip without debate
3Genuine stump — model failure caused by video content difficulty, not prompt ambiguity

Sample Task — The Woman in Green (18-Criterion Rubric)

Prompt tracked fine-grained physical actions performed by Dr. Watson under hypnosis across a 66-second window [52:07–53:13], synchronized against Dr. Onslow's verbal commands.

14 positive criteria: atomic action sequence — stands up, turns, guided to chair, lifts left leg, pivoted 90°, left foot on chair, mimics untying, slips shoe off, removes sock, rolls trouser leg, right foot on chair, removes right foot, turns around, sits back down
4 negative criteria: hallucination guards — did not untie shoe, did not roll both trouser legs, did not remove jacket, no unlisted actions attributed

Why Models Failed

Wrong foot / side confusion Hallucinated untying action Audio-visual desync Fine-grained action omission

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
🗺️Backwards construction: answer-first → prompt design
📄Atomic fact fan-out with per-URL verification

AI Task Designer — Contract

Stellar AI

Project-Based Remote
  • Built agentic evaluation tasks on the Lynx platform — designed task scenarios and task motivation (what makes the prompt difficult for the AI), selected 5+ tools per scenario (Salesforce, Google Calendar, Gmail, Contacts, SMS), generated realistic mock databases, and tagged required skills and capabilities from a standardized taxonomy
  • Authored Golden Trajectory (GT) projects: wrote prompts engineered so the model fails initially, then authored progressive hint sequences until the model passes — success required both a genuine failure and a hint-guided recovery
  • Authored Developer Instruction (DI) projects: wrote prompts the model passes cleanly, then crafted developer instructions that force a legitimate failure — success required both an initial pass and an instruction-induced fail
  • Compared model outputs against expected outcomes, built verification rubrics for each scenario, and submitted completed tasks through automated consistency checks — rebuilding scenarios from downstream when checks flagged issues

AI Task Designer — Contract

Handshake AI

Project-Based Remote
  • Authored web-source golden trajectories for RLHF/SFT training data, working backwards from deterministic answers to construct multi-hop reasoning chains across 5–8 niche, non-indexed URLs spanning unrelated domains
  • Designed prompts using attributes and anchors (never specifics), requiring models to traverse history, geography, law, and academia to extract a single verifiable answer — with at least 1 of 8 model runs required to fail
  • Wrote per-URL step-by-step verification explanations, decomposed into atomic facts (fan-out) that each map to a specific source location — used to build the golden trajectory and evaluation rubric
  • Navigated 10–15+ QA checkpoints per task: ambiguity checks, unnecessary constraint checks, source validation, URL verification, and automated model failure confirmation
  • Contributed to Project Voyager — multimodal video evaluation track — authoring rubric-based prompts that required genuine audio-visual integration to answer, with 18-criterion rubrics and negative hallucination guards to expose fine-grained model failure modes

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
  • Managing the full sales cycle: lead generation, needs-based analysis, quoting, policy binding, and post-sale client servicing
  • Launched lainsurancequotes.com — a self-built digital branding and lead generation platform designed to capture and qualify local agency prospects
  • Navigated corporate onboarding processes, IFR documentation, and retention initiatives with precision and compliance

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 evaluation scenarios and training data.

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
  • Managed full sales cycle: lead generation, needs-based analysis, quoting, policy binding, and post-sale client servicing
  • Trained team members on Salesforce optimization (lead prioritization, tracking, data integrity) to deliver a 20% productivity lift
  • Maintained 80%+ Drive Safe & Save setup rate and engineered lead provider partnerships (QuoteWizard, ZipQuote) to boost lead flow by 20%
  • Navigated corporate processes including onboarding, IFR documentation, and retention initiatives with precision and compliance
How this builds AI skills →

CRM architecture, workflow automation, team training on technical tools, and data-driven funnel optimization — directly transferable to AI evaluation design and rubric-based quality systems.

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 via 100+ daily outbound consultative calls, and managed social ad campaigns (Facebook, Instagram, LinkedIn) delivering consistent 20%+ ROI
  • Configured and optimized Prospector+ CRM (market segmentation, performance dashboards, bonus structures) and designed automated multi-touch drip campaigns via Agent Advertise System
  • Synthesized performance metrics across Prospector+, Agent Analytics, and Control-D to identify trends, recalibrate marketing strategy, and provide leadership with actionable insights
How this builds AI skills →

Marketing automation, CRM segmentation, and analytical tool configuration — foundational logic for designing structured evaluation workflows and training data pipelines.

Level 3 Internet Support Specialist

CenturyLink

Oct 2006 — Nov 2011 Monroe, LA
  • Diagnosed complex DSL connectivity and hardware issues using Adtran systems (line cards, SNR margins, port configurations) and executed system-level diagnostics to identify faults
  • Managed DNS infrastructure (A, PTR, NS records) and resolved IP conflicts via DHCP server administration, monitoring real-time negotiations to prevent latency or routing failures
  • Translated complex technical network diagnostics into clear, jargon-free guidance to accelerate issue resolution and improve client satisfaction

Network Support Specialist

Bayou Internet

Jun 2005 — Oct 2006 Monroe, LA
  • Resolved network issues (DSL, VoIP, IPTV, email) and conflicts for technicians, and supported **wireless AP/mesh node deployments** with clear documentation
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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.

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Producer License, Individual

Insurance Certification · License #LA-867875

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