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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

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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

How I AI

2025/12/15
How I AI

How I AI

2025/12/15
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

Cortney Hickey is the executive assistant to the CEO at Zapier, where she’s leveraging AI to transform traditional EA responsibilities into scalable, organization-wide systems. In this episode, she demonstrates how she’s built AI workflows that automate meeting preparation, reinforce company culture through automated feedback, and democratize strategic knowledge across the organization. Her approach shows how EAs can use AI not to replace their roles but to elevate them—working on higher-impact initiatives while creating systems that benefit the entire company. What you’ll learn: 1. How to build an automated meeting prep system that researches participants, checks CRM data, and delivers actionable insights before important meetings 2. A framework for creating AI-powered culture reinforcement through automated meeting feedback aligned with company values and operating principles 3. How to develop an AI-powered document review system that helps teams align with executive expectations before formal reviews 4. A strategy for creating a centralized knowledge base that makes company strategy accessible and interactive for all employees 5. Why “progress over perfection” is the key mindset for building effective AI workflows that evolve over time 6. How EAs can use AI automation to work themselves out of repetitive tasks and into higher-impact strategic roles — Brought to you by: WorkOS [https://workos.com/?utm_source=lennys_howiai&utm_medium=podcast&utm_campaign=q22025]—Make your app enterprise-ready today Brex [https://brex.com/howiai]—The intelligent finance platform built for founders — In this episode, we cover: (00:00) Introduction to Cortney (02:48) Overview of meeting prep automation with Zapier Agents (04:43) How the meeting prep agent works (10:21) An example of the meeting prep agent in practice (12:16) Creating a culture reinforcement system through meeting feedback (15:45) EAs’ unique position to leverage these tools (18:12) Building an automated meeting coach (24:03) Developing an executive document review system (33:15) Creating a centralized strategy companion in NotebookLM (36:18) How AI is transforming the EA role, not replacing it (40:00) Lightning round and final thoughts — Tools referenced: • Zapier: https://zapier.com/ [https://zapier.com/] • Zapier Agents: https://zapier.com/agents [https://zapier.com/agents] • Todoist: https://todoist.com/ [https://todoist.com/] • Slack: https://slack.com/ [https://slack.com/] • HubSpot: https://www.hubspot.com/ [https://www.hubspot.com/] • ChatGPT: https://chat.openai.com/ [https://chat.openai.com/] • Google NotebookLM: https://notebooklm.google/ [https://notebooklm.google/] — Where to find Cortney Hickey: LinkedIn: https://www.linkedin.com/in/cortneyhickey/ [https://www.linkedin.com/in/cortneyhickey/] — Where to find Claire Vo: ChatPRD: https://www.chatprd.ai/ [https://www.chatprd.ai/] Website: https://clairevo.com/ [https://clairevo.com/] LinkedIn: https://www.linkedin.com/in/clairevo/ [https://www.linkedin.com/in/clairevo/] X: https://x.com/clairevo [https://x.com/clairevo] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email jordan@penname.co.

Highlights

In this episode, Cortney Hickey shares how she’s harnessing AI to reimagine the role of the executive assistant, turning administrative workflows into scalable systems that benefit the entire organization. Rather than simply automating tasks, she demonstrates how intelligent tools can amplify human judgment, enhance strategic alignment, and foster a more cohesive company culture.
01:30
AI can think like a human and handle repetitive tasks effectively
02:49
Using AI in my role as an EA is inevitable.
07:39
The agent checks CRM and communication history to provide context-aware meeting prep recommendations
10:23
The AI agent reveals its thinking process, including calendar checks and participant research in HubSpot.
12:16
AI agents can learn over time like interns and be shared as customizable templates.
18:12
Create a 'Ron Swanson agent' to reschedule all meetings for maximum efficiency
18:13
The Fellow agent was adjusted to balance supportive and demanding feedback based on executive input
27:54
Exec Prep GPT provides feedback on meeting documents, suggests rewrites, and can eliminate unnecessary meetings.
33:15
The tool can auto-generate content like podcasts from strategy documents
36:19
AI won't replace EAs but enables them to focus on creative and relationship-driven tasks
40:13
Use direct, rambling feedback when AI doesn't meet expectations

Chapters

Introduction to Cortney
00:00
Overview of meeting prep automation with Zapier Agents
02:48
How the meeting prep agent works
04:43
An example of the meeting prep agent in practice
10:21
Creating a culture reinforcement system through meeting feedback
12:16
EAs’ unique position to leverage these tools
15:45
Building an automated meeting coach
18:12
Developing an executive document review system
24:03
Creating a centralized strategy companion in NotebookLM
33:15
How AI is transforming the EA role, not replacing it
36:18
Lightning round and final thoughts
40:00

Transcript

Cortney Hickey: 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. Claire Vo: I think this is going to...