Tool · AI Agents · Cursor

JobbyBobby

A multi-agent AI system for running a high-intensity job search with a hard deadline. Built and operated entirely inside Cursor with Claude.

Four agents working in parallel to organize, scout, advise, and build.

How It Works

Each message sent in the project triggers a timestamp check. If an agent is overdue, it fires automatically before responding to whatever was asked. No background timers — the check runs the moment you type anything. The whole system lives in a .claude/ folder alongside the job tracking files.

The Agents

Four agents, one shared context, one goal.

Bobby

Master Organizer

Runs a status check every 24 hours. Tracks applications, flags duplicates, and keeps the file system clean. The source of truth.

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Lois

Daily Job Scout

Scans job boards every 24 hours. Evaluates fit across six active career lanes, filters by location and salary, and queues new leads for review.

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Architect

Technical Lead

Handles hands-on implementation: website updates, utility scripts, and anything that requires actual code. Invoked manually.

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Advisors

Strategic Counsel

Three advisors: Sammy (small studio / Lane A), Larry (big studio / Lane C and transition roles), Compass (career + life coach). All read the full dossier before advising.

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Six Active Career Lanes

The transition sprint runs across six distinct, non-overlapping targets.

Lane A

Creative Technology & Prototyping — High

Hands-on AI production, visual R&D, and rapid prototyping.

Lane C

Senior Art & Art Leadership — Safety net

Senior craft and leadership with pipeline awareness, not traditional TA.

Lane D

AI Evaluation & Quality Operations — High

AI training, multimodal evaluation, rubrics, and reviewer quality.

Lane E

Product / UX Design — Transition

Visual-product craft, prototyping, UX process, and systems thinking.

Lane F

Teaching & Creative Education — Supplemental

Instruction, workshops, portfolio review, and creative mentoring.

Lane G

Creative Operations & Program Delivery — Primary

Resourcing, vendors, budgets, schedules, and cross-functional delivery.

Built With

CursorClaude (Anthropic)Markdown filesNo backendNo database