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How Zapier’s EA built an army of AI interns to automate meeting prep, strengthen team culture, and scale internal alignment | Cortney Hickey

44 min episode · 2 min read
·
Clara Vaux,Cortney Hickey

Episode

44 min

Read time

2 min

Topics

Remote Work, Relationships, Leadership

AI-Generated Summary

Key Takeaways

  • Weekly Meeting Prep Agent: Automated Friday workflow researches external meeting participants via web search, checks CRM relationships in HubSpot, scans Gmail and Slack history, then creates Todoist tasks two hours before meetings and delivers structured Slack digest with prep recommendations.
  • Automated Meeting Feedback System: Post-meeting agent analyzes transcripts against company values and Five Dysfunctions of a Team framework, sends direct Slack feedback to all participants highlighting one to two growth opportunities, normalizing continuous feedback without ego threat from human managers.
  • Executive Prep GPT: Custom ChatGPT trained on company strategy memos, team norms, and past feedback helps employees stress-test documents before executive review, resulting in 278 users sharpening strategy docs, reducing meeting bottlenecks, and sometimes eliminating meetings entirely when clarity is achieved.
  • Strategy Companion in NotebookLM: Knowledge base containing dozens of sources including strategy documents, all-hands transcripts, and org action plans allows employees to query how their role connects to company strategy, with auto-generated podcast summaries making strategy interactive rather than static.

What It Covers

Cortney Hickey, EA to Zapier's CEO, demonstrates how she built AI agents to automate meeting preparation, enforce company cultural values through automated feedback, and scale strategic alignment across the organization.

Key Questions Answered

  • Weekly Meeting Prep Agent: Automated Friday workflow researches external meeting participants via web search, checks CRM relationships in HubSpot, scans Gmail and Slack history, then creates Todoist tasks two hours before meetings and delivers structured Slack digest with prep recommendations.
  • Automated Meeting Feedback System: Post-meeting agent analyzes transcripts against company values and Five Dysfunctions of a Team framework, sends direct Slack feedback to all participants highlighting one to two growth opportunities, normalizing continuous feedback without ego threat from human managers.
  • Executive Prep GPT: Custom ChatGPT trained on company strategy memos, team norms, and past feedback helps employees stress-test documents before executive review, resulting in 278 users sharpening strategy docs, reducing meeting bottlenecks, and sometimes eliminating meetings entirely when clarity is achieved.
  • Strategy Companion in NotebookLM: Knowledge base containing dozens of sources including strategy documents, all-hands transcripts, and org action plans allows employees to query how their role connects to company strategy, with auto-generated podcast summaries making strategy interactive rather than static.

Notable Moment

The CEO requested tougher automated feedback after initial versions were too soft, leading to AI-generated coaching that directly calls out issues like fear of conflict and slow decision-making, which employees accept more readily than human criticism.

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Episode Transcript

I think from EAs I hear like, oh, AI doesn't think the way I do. I'm like, it can though. It can. As long as you can figure out the system behind why you're doing things and be able to articulate that. I think this is going to be one of the most practical, time saving, and stress saving episodes of how IAI we have ever had. This agent does everything you want and then more. And over time, you can make it more intelligent. It's serving as this kind of second brain for me where yes, I have all this and part of my superpower as an EA is remembering all these things about people. But this is making sure that it's not all in my head and I can really refresh my memory quickly on all the context rather than diving through through the CRM, my email, Slack, and looking at all these things separately. If you are doing a repeated task every week, spend time that week automating that task. I definitely am a believer that AI can only enable us in this role. I think it's a when, not an if. We will have to be folks that adopt these tools. Welcome back to How I AI. I'm Clara Vaux, product leader and AI obsessive here on a mission to help you build better with these new tools. Today, we have Courtney Hickey, EA to the CEO at Zapier. And, yes, of course, she uses AI to automate all of the admin tasks related to meetings and document preps and feedback, but she's also gonna show us some unique ways that you can use AI to reinforce your cultural values and operating principles. This is a really great one for anybody thinking about organization at scale, operations at scale, and culture at scale. Let's get to it. This episode is brought to you by WorkOS. AI has already changed how we work. Tools are helping teams write better code, analyze customer data, and even handle support tickets automatically. But there's a catch. These tools only work well when they have deep access to company systems. Your Copilot needs to see your entire code base. Your chatbot needs to search across internal docs. And for enterprise buyers, that raises serious security concerns. That's why these apps face intense IT scrutiny from day one. To pass, they need secure authentication, access controls, audit logs, the whole suite of enterprise features. Building all that from scratch, it's a massive lift. That's where WorkOS comes in. WorkOS gives you drop in APIs for enterprise features so your app can become enterprise ready and scale up market faster. Think of it like Stripe for enterprise features. OpenAI, Perplexity, and Cursor are already using Work OS to move faster and meet enterprise demands. Join them and hundreds of other industry leaders at workos.com. Start building today. Courtney, welcome to How I AI. I am really excited about this episode because I think …

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Books, tools, and gear mentioned in this episode

SignalCast may earn commission on purchases via these links. As an Amazon Associate, SignalCast earns from qualifying purchases.

Books

Tools

  • Strategy Companion in NotebookLM: Knowledge base containing dozens of sources including strategy documents
  • creates Todoist tasks two hours before meetings
  • checks CRM relationships in HubSpot
  • Custom ChatGPT trained on company strategy memos, team norms, and past feedback

company

  • SPONSORS: Brex, brex.com/howiai
  • SPONSORS: WorkOS, workos.com

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