Personal AI fluency, the Master Context Doc, and the move from one-off prompts to scheduled automation — Ryan Staley's working session for ~260 GTM operators.
Today's class shifted gears from theory to hands-on. Ryan walked the cohort through building a Master Context Doc — your company, ICP, value prop, case studies — that becomes the spine every Claude session reads from. The move he kept driving home: stop typing one-off prompts. Build a personal context layer once, then use Claude Code's plan mode to design repeatable workflows. Pair that with the right model for the job (Opus to plan, Haiku to execute) and the unit economics of AI in your week change overnight.
Ryan refined this curriculum across 3,000+ operators over three years. The order matters — fluency is the prerequisite to cascade is the prerequisite to apply.
You can't lead a team through AI if you can't run your own desk with it. Step one is building a personal context layer the model can read every session — your role, your ICP, your competitors, your differentiator. Without it, every prompt starts at zero.
"Don't multitask. This is going to seem like it's going at breakneck speed. If you're trying to type emails or do other stuff, you're going to miss out on a ton."
Once your own workflow runs on AI, the next move is to cascade it — to your team, to the function, to the company. The Master Context Doc isn't just yours. It becomes the shared spine your VPs and managers point their own Claude sessions at, so every output speaks the same brand voice.
Fluency + cascade only matter if they show up in pipeline. The hands-on portion focused on applying the system to real GTM jobs: daily planning automation, outbound research, deal strategy. The principle: pick one workflow, automate it end-to-end, then move to the next.
Quick start-of-class poll on primary model. Compared to the January cohort, Claude's dominance has grown — and ChatGPT's primary-tool share has compressed dramatically.
| Primary model | Q2 2026 cohort | Where it wins | Ryan's take |
|---|---|---|---|
| Claude | 80% | Long-form reasoning, agentic work, Cowork's structured projects, Claude Code for terminal-driven automation | The default for almost everyone in the room. Pair Opus (plan) with Haiku (execute) for cost. |
| ChatGPT | 10% | Image generation, voice mode, broadest plugin ecosystem | Still useful but the cohort has shifted. Use it for what it's best at, not as the default. |
| Gemini | 6% | Google Workspace integration, long-context document analysis, NotebookLM | "Underused. If you live in Workspace, the security envelope alone is worth it." |
| Copilot / others | ~4% | Microsoft 365 enterprises with data-privacy constraints | Default if you're already a Microsoft shop — Copilot has Claude under the hood. |
A single markdown file that travels into every Claude session and tells the model who you are, what you sell, and how you sell it. Ryan walked through it live; here's the structure.
Role, company, what you actually do day-to-day. Three sentences. The model doesn't need a resume — it needs the lens.
One paragraph product description. Target buyer title. Average deal size. Sales cycle length. Pricing model. Anything that anchors the model in your real economics.
Industries, company size, the signals that mean "good fit." Equally important: who's not your ICP and why. The model needs both halves to triage effectively.
Top 3–5 competitors, one sentence each on how you position against them. This is the layer that makes the difference between generic AI output and feels-like-our-team output.
Two or three real customer outcomes — the named account, the problem, the numerical result. The model uses these as anchors for tone, depth, and specificity.
CRM, outreach platform, enrichment, conversation intelligence. The model needs to know what it can suggest and what it can't.
Ryan ran two live builds — both starting from the Master Context Doc, both using Claude Code in plan mode.
A cohort question opened up the most concrete cost lever Ryan surfaced all session.
Ryan's homework for the room — concrete, finite, and doable in a single Sunday afternoon.
CLAUDE.md if you're in Claude Code; pin it as a Project in Cowork.