LEARN · Intro Fundamentals ★ Entry 1
Intro Fundamentals
▸Start here · self-paced · open to everyone
Orientation
The AI Landscape
Set up
Introductions
Week 1 · Foundations
The AI Mindset
The Road Ahead
What Is Generative AI?
AI Is Your New Colleague
Autocomplete on SteroidsFree preview
Pre-Training: The Prediction Machine
Post-Training: Teaching It to Chat
Context Is Everything
What Can Go Wrong?
Prompting with C-R-I-T
Security
Key Takeaways
Week 2 · Prompting in practice
Wins & Stuck Points
Why Your Prompt Missed
The Interview Step
Role Engineering
Numbers Beat Adjectives
The Translation Problem
Build Your Translation Prompt
The Refine Loop
Your Inbox, Your Voice
Map It to Opportunities
Your Master Document
I
Checkpoint I
Unlocks Weeks 3 and 4
▾▾Unlocked by completion of Checkpoint I
Week 3 · Daily habits
5-minute morning AI ritual
AI for inbox triage
AI for meeting prep
Meeting follow-up & actions
AI for writing (draft/edit/proof)
AI for research (first pass)
AI for explaining things
AI for decisions (brief the call)
"Five whys" with AI
Week 4 · Patterns
Recurring task → reusable template
Zero/one/few-shot (no jargon)
Persona prompting
Reverse prompting
Prompt chaining
Iterate vs start over
"Show me bad examples" trick
"Draft a response" pattern
"Rewrite in my voice" pattern
II
Checkpoint II
Unlocks Weeks 5 and 6
▾▾Unlocked by completion of Checkpoint II
Week 5 · Tools & formats
Working with images
Working with documents
Working with spreadsheets
Voice-to-AI
AI on your phone
"Simplify this" pattern
"What am I missing" pattern
"Make it shorter" pattern
"Make this presentable" pattern
Week 6 · Habit & capstone
Comparing AI tools side-by-side
Your personal prompt library
Team prompt vault (intro)
Context windows explained
Build your daily AI habit
Better, not only faster
The AI confidence trap
Recovering from a bad session
Explaining AI work to colleagues
Commitment: one weekly prompt
Capstone: automate one task
III
Checkpoint III
Fundamentals complete → Cohort Cowork
LEARN · Cohort Cowork
Cohort Cowork
Requires completion of Intro Fundamentals
Vocab & workflow audit
Shared vocab & mental model
Workflow audit: where AI fits
Claude Desktop + connector setup
Prompt library & cowork sprints
The shared prompt library
Cowork sprints on live workflows
Build-vs-buy: informed buyer
Champion model & MCP literacy
The internal champion model
MCP & connector literacy
ROI measurement & showcase
Measuring AI ROI at team level
Showcase + project scoping
✓
Cohort Badge
Cohort Cowork complete
BUILD · Project Build
Project Build
Requires completion of Cohort Cowork
Scope
ROI filter: pick the right first build
Triggers, actions, data pipelines
MCP servers & webhooks 101
Design
Build Your Own Task Manager
Build Your Own CRM
Build
Custom agents: scope → build → deploy
Human-in-the-loop workflows
Cost, latency & reliability
Ship
AI evaluations: testing outputs
Showcase + handoff docs
✓
Project Badge
Project Build complete
ONGOING · Partnership
Ongoing Partnership
Requires completion of Project Build
Onboard & integrate
Monthly "What's new in AI" briefing
Single agent strategy
New hire AI onboarding
Embedded buildout support
Quarterly cadence
Multi-agent systems
Coordinated agents & orchestration
Quarterly skills-gap assessment
Risk & renewal
Risk & oversight (ongoing)
Change mgmt: skeptic & overuser
Annual AI strategy + budget
✓
Partner Seal
Partnership active
ONGOING · Long-term Advisor
Long-term Advisor
Requires completion of Ongoing Partnership
Annual strategy
Annual strategy roadmap (board)
Industry positioning: AI moat
AI-native org design review
Founder strategy session w/ Sean
Co-marketing
Case study + co-marketing
Early access to CrossGen pilots
Mentor track: teach new cohorts
Peer network
Alumni roundtables (CEO/COO)
Talent strategy: AI-augmented hiring
M&A diligence: AI capabilities audit
✓
3-Yr Seal
Long-term
Rank ladder · earned by submitting The Crossing (your shipped artifact)
Gen-0 · NewcomerDefault on join
Gen-1 · AI OperatorSubmit 3 Intro artifacts
Gen-2 · AI BuilderSubmit 4 Intermediate artifacts
Gen-3 · AI ArchitectSubmit 2 Advanced artifacts
Gen-4 · AI ForerunnerMentor + co-host events · CrossGen alumni
★ INTRO
▸Open to Gen-0 · everyone
The CRIT Method · Engineering Your AIBuild a CRIT prompt library
AI as Your New Intern · The Manager MindsetLog 10 managed-AI cases
Daily AI HabitsRun "My AI day" for 14 days
Grounding AI in Your Own FilesWrite a 1-page cited briefing
AI for Writing & EditingBuild a before/after writing pack
★★ INTERMEDIATE
Requires Gen-1 · submit 3 Intro Crossings
Controlling Probability · Hallucinations & ContextCatch and fix 5 hallucinations
Inbox & Email AutomationBuild an inbox assistant + 2-week log
Meetings & Notes IntelligenceRun your workflow on 3 meetings
Claude Projects · Your Custom AssistantBuild a Project + 5 real uses
Spreadsheets, Data & AnalysisClean a dataset + write the memo
Marketing & Content WorkflowsTurn 1 idea into 4 content pieces
Customer-Facing AIShip a live customer workflow
Skills Library · Reusable WorkflowsBuild 5+ Skills + a usage log
Accidental Coding · Reading Code Without FearShip a Claude Code script
AI Security & Responsible UseWrite an AI use policy + run an audit
★★★ ADVANCED
Requires Gen-2 · submit 4 Intermediate Crossings
Prompt Chaining & The Editor PatternChain 3 real tasks end to end
Artifacts & Live DeliverablesBuild 3 live artifacts
End-to-End Agentic Workflows in ClaudeShip a verified agentic workflow
🎟 LIVE IN-PERSON EVENTS
Build Your Own AI Daily HabitGen-1
Build Your Own Inbox TriageGen-2
Build Your Own Claude ProjectGen-2
Build Your Own CRMGen-3
Build Your Own Custom AgentGen-3
Co-host a Live Event with CrossGenGen-4
On-prem AI core
WHAT IT IS
NVIDIA Hardware systems for on-prem AI: private RAG, self-hosted agents, production deployment of what you built in CrossGen.
WHY IT MATTERS
Data sovereignty. Predictable cost at scale. Regulated industries. Speed without API limits.
WHO IT'S FOR
Independent learners ready to deploy locally, OR partners with sensitive workloads.
Cards with the ◧ green edge across the other trees are Hardware-eligible. These are classes where Hardware changes what's possible, not only how.