An Outpost Program · NYC
The certification behind every AI-native Outpost hire.
Outpost University is the rigorous 10-week program every Outpost team member completes before they touch client work. We don't just train on prompts — we build operators fluent in RAG, MCP, agents, and evals.
ProgramOutpost AI Operator
Duration10 weeks · 6–8h / wk
CohortRolling start
OutcomeProbation gate
The 10-Week Syllabus
v.1.0 — working draft01
AI 101: What AI Actually Is
How LLMs actually work — transformers, tokens, hallucinations, and the current model landscape.
Foundations
02
Prompt Engineering Fundamentals
The anatomy of a strong prompt and how to debug failure modes systematically.
Prompting
03
Daily Drivers: Claude, ChatGPT, Cursor
When to reach for Claude vs. ChatGPT vs. Cursor — speed, depth, and tool access trade-offs.
Tooling
04
Context, Memory, and Skill Files
Context windows, project knowledge, and turning a general model into a domain specialist with Skill files.
Context Engineering
05
RAG: Retrieval-Augmented Generation
Vector embeddings, when to RAG vs. paste context, and building a working pipeline end-to-end.
Systems
06
MCP and Tool Integration
Model Context Protocol, function calling, and building a connected workspace.
Integration
07
Agents and Orchestration
The agent loop — plan, act, observe, repeat — and when to build an agent vs. a workflow.
Automation
08
Evals: Knowing Your AI Actually Works
Why evals matter, how to write them, and how they wire into client deliverables.
Quality
09
Function-Specific Deep Dive
Track A: Data & AI · Track B: Finance & Ops · Track C: Marketing & Brand · Track D: Search Ops & BD.
Specialization
10
Capstone, Demo Day, and Operating Manual
Polish the capstone, present at Demo Day, and codify your operating system for the rest of the firm.
Output
Social Proof of Competence
The Outpost AI Operator credential.
Every graduate ships a working AI capstone, an eval suite, and a Personal AI Operating Manual contributed to the firm playbook. The credential is verifiable on a public URL — clients, recruiters, and collaborators can confirm any operator's work in one click.
10
Weeks of build challenges
2+
AI techniques per capstone
100%
Bar to clear probation
Outpost
Certification of Proficiency
Operator Name
Track: Data & AI Engineering · Class of 2026
Verifiable at
outpost-university/verify/—
Director Signature
Operators deployed at
Shore Capital PartnersThe Princeton Review+ private equity & search-fund partners