Automate Your Entire Work Life With Claude Code — No Coding Needed

Dave Killeen is the Field CPO at Pendo.io with 25 years in product. He built a personal operating system called DEX in Claude Code that runs his entire workday from one terminal command, pulling from his calendar, CRM, meeting notes, LinkedIn, YouTube, and 120 newsletters. In this episode, he walks through the full system live on screen and shows you how to build your own. Full Writeup: https://www.news.aakashg.com/p/dave-killeen-podcast Transcript: https://www.aakashg.com/the-personal-operating-system-from-pendos-field-cpo/ DEX: https://heydex.ai/ --- Timestamps: 0:00 - Intro 1:47 - Live demo of the daily plan command 5:43 - Daily plan output and account intelligence 10:13 - Ads 11:53 - Claude Code terminal vs Cursor 16:46 - From backlog idea to a full PRD 21:42 - The Claude MD file walkthrough 25:02 - Kanban board for managing PRDs 28:38 - Career planning with the career MCP server 31:00 - Ads 33:42 - Skills vs MCP servers vs hooks explained 36:36 - Intelligence scanning across YouTube and newsletters 40:11 - Hooks deep dive and session start hooks 44:58 - Pi, Open Claw, and LLM-neutral agents 49:02 - What is overhyped vs underhyped in AI tooling 52:14 - Outro --- 🏆 Thanks to our sponsors: 1. Pendo: The #1 software experience management platform - http://www.pendo.io/aakash 2. Jira Product Discovery: Plan with purpose, ship with confidence - https://www.atlassian.com/software/jira/product-discovery 3. Amplitude: The market-leader in product analytics - https://amplitude.com/session-replay?utm_campaign=session-replay-launch-2025&utm_source=linkedin&utm_medium=organic-social&utm_content=productgrowthpodcast 4. NayaOne: Airgapped cloud-agnostic sandbox - https://nayaone.com/aakash/ 5. Product Faculty: Get $550 off the AI PM Certification with code AAKASH550C7 - https://maven.com/product-faculty/ai-product-management-certification?promoCode=AAKASH550C7 --- 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. --- 👨‍💻 Where to find Dave Killeen: LinkedIn: linkedin.com/in/davekilleen X: https://x.com/thevibepm Pendo: https://www.pendo.io DEX: https://heydex.ai/ 👨‍💻 Where to find Aakash: Twitter: https://www.x.com/aakashg0 LinkedIn: https://www.linkedin.com/in/aakashgupta/ Newsletter: https://www.news.aakashg.com #claudecode #aipm --- 🧠 About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. 🔔 Subscribe and turn on notifications to get more videos like this.

Aakash GuptahostDave Killeenguest

Mar 10, 202652mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Build a personal operating system using Claude Code and Dex

Dave runs a single “daily plan” command that automatically aggregates calendar, goals, meeting notes, CRM/deal intel, and market signals into a prioritized plan with drafted follow-up messages.
Dex is built around plain-text/Markdown “living files” that continuously compound in usefulness as new meetings, tasks, and insights are appended and cross-linked to projects, people, and accounts.
The workflow extends beyond planning into product execution: ideas are ranked in a backlog, expanded into PRDs, and managed through a lightweight Kanban UI that Claude can advance autonomously.
The technical backbone is clarified: skills/commands describe repeatable jobs, MCP servers provide deterministic guardrails for integrations, and Claude Code hooks (especially session-start) enforce reliable context injection and learning from mistakes.
Killeen argues the differentiator vs. ChatGPT-style chats is persistence and compounding context, while emphasizing “taste” (human judgment) to avoid overwhelm and low-quality output at scale.

IDEAS WORTH REMEMBERING

5 ideas

One command can replace hours of context gathering—if your data is wired in.

Killeen’s daily plan pulls from calendar, quarterly/weekly goals, meeting transcripts (Granola), CRM/deal tools (e.g., Clari), newsletters, YouTube, and LinkedIn to produce priorities and even drafted Slack outreach.

“Living files” are the compounding advantage over chat-only AI.

By appending new evidence (meeting actions, stakeholder updates, account changes) to project/person/company pages, future sessions become smarter and faster without relying on opaque model memory.

Use MCP servers when you need reliability and repeatability.

Skills/commands can be probabilistic, but MCP servers enforce tighter, more deterministic interaction patterns with external systems (e.g., consistent task creation rules, safe data access patterns).

Claude Code hooks are what make the system feel persistent and self-improving.

Session-start hooks can inject weekly priorities, strategic pillars, preferences, and past mistakes into every new chat—reducing regressions and keeping work aligned without manually re-briefing the model.

PRDs are now cheap—attention management becomes the real bottleneck.

Generating many parallel PRDs creates cognitive overhead, so Killeen built a Kanban-style UI that scores, ranks, and suggests next actions to keep execution manageable.

WORDS WORTH SAVING

5 quotes

So I run one command in the morning, and five minutes later I know what deals need attention, who I'm meeting, what I owe them, and what they owe me. And I didn't gather any of it.

— Dave Killeen

Everything compounds. All the files get smarter and smarter. They're living files.

— Dave Killeen

MCP is better for AI than the APIs… it acts as better guardrails for the AI.

— Dave Killeen

Hooks are magical and really changes how you use Claude Code.

— Dave Killeen

It’s a bit like we’re all Michelin head chefs… we design the menu, and we have the AI chefs in the kitchen doing it for us.

— Dave Killeen

Daily plan automation across tools (calendar/CRM/meetings/newsletters)Markdown-based “living files” and personal knowledge managementMCP servers as integration guardrails vs APIsSkills/commands library and X-ray (mermaid diagram) explainabilityClaude MD file, progressive disclosure, and version controlClaude Code hooks (session start, mistakes/preferences capture)From backlog ideas to PRDs to Kanban execution

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