Compounding Context with Living Files

Today’s episode

Most PMs start every day like this. Open the calendar. Open the CRM. Open Slack. Open the meeting notes. Open LinkedIn. Piece together what matters. Lose 30 minutes before real work even starts.

That is not how the best PMs are working anymore. The best PMs are running one command in the morning and getting everything they need in five minutes. Their calendar, their deals, their market intel, their career gaps, all pulled together automatically.

That shift is what today’s episode is about.

I sat down with Dave Killeen, Field CPO at Pendo.io. He has worked at BBC, Mail Online, and now runs the field product function at one of the largest product management platforms in the world. He has 25 years in product. Over the last few months, he built a full personal operating system called DEX in Claude Code, open sourced it on GitHub, and it is getting serious traction.

In this conversation, Dave walks through his entire system live on screen. You will see how he runs a daily plan, creates PRDs from a backlog, manages parallel workstreams on a Kanban board, and tracks his career goals, all from one terminal window. And you will learn the three building blocks that make it all work.

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Check out the conversation on Apple, Spotify and YouTube.

Brought to you by

* Pendo: The #1 software experience management platform

* Jira Product Discovery: Plan with purpose, ship with confidence

* Amplitude: The market-leader in product analytics

* NayaOne: Airgapped cloud-agnostic sandbox

* Product Faculty: Get $550 off the AI PM Certification with code AAKASH550C7

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Key Takeaways:

1. One command replaces your morning routine - Dave's daily plan slash command pulls from calendar, CRM, Granola, LinkedIn, YouTube, and 120 newsletters in five minutes. No tab switching. No manual assembly.

2. MCP servers are the key to connecting everything - Point Claude at any API documentation with your API key and it builds an MCP server for you. MCP provides structured guardrails that make the AI's behavior consistent and deterministic.

3. Skills, MCP, and hooks are three different things - Skills are plain English job descriptions for what the AI should do. MCP servers are structured integrations for connecting external services. Hooks are triggers that fire at specific conversation moments.

4. Session start hooks make the system compound - Every new Claude Code chat gets injected with weekly priorities, quarterly goals, working preferences, and past mistakes. The AI never starts from scratch.

5. Living markdown files are the compounding mechanism - Every project, person, and company gets a markdown file that accumulates context from meetings, messages, and intel over time. The more you use the system, the smarter every file becomes.

6. You can build a mobile app in 37 minutes - Dave built the full app with Claude and spent more time in Xcode publishing it. The constraint is taste, not building speed.

7. The AI should hold you accountable - Dave's Claude MD file includes "harsh truths for Dave" that the AI wrote after auditing his system. This gets injected into every session to prevent the same mistakes.

8. Career planning should compound like product data - A career MCP server collects evidence, runs gap analysis, and calculates promotion readiness. When review time comes, the evidence is already assembled.

9. Be precise about your goal, not the path - The kindest thing you can do for the AI is give it a very clear destination. Do not tell it how to get there. Let it figure out the most elegant approach itself.

10. Voice-first changes everything - Using Whisperflow or Super Whisper instead of typing fundamentally changes how you interact with Claude. You think out loud. The conversation flows. You build faster.

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Where to find Dave Killeen

* LinkedIn

* Pendo

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Related content

Newsletters

* The PM operating system guide

* How to use Claude Code like a pro

* Master AI agent distribution

* Claude Cowork and Code setup guide

* The AI PM tool stack

Podcasts

* Frank Lee on Claude Code and MCP workflows

* Carl Vellotti on Claude Code operating systems

* Rachel Wolan on AI PM workflows

* Caitlin Sullivan on building with Claude

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