AI in the Chief of Staff's Toolkit #NYTechWeek

Hosted by Ask a Chief of Staff and Notion This event is a part of #NYTechWeek—a week of events hosted by VCs and startups to bring together the tech ecosystem. Learn more at www.tech-week.com In this panel discussion, we'll dive into how these strategic operators are leveraging tools like Notion and AI to streamline systems, drive execution, and support their founders as true force multipliers. What we’ll cover: ✅ Building a tech stack that grows with your company; ✅ Real examples of how Chiefs of Staff use Notion to manage projects, docs, and knowledge; ✅ Where AI tools are helping—and where they’re overhyped; ✅ Lessons learned from supporting founders through rapid growth; ✅ Favorite templates, tools, and workflows from the trenches Panelists: ✨ Kyle Hagge, Chief of Staff at Morning Brew ✨ Rachel Chung, Chief of Staff at Wagmo ✨ Stacy Oentero Ward, Chief of Staff at Skillit ✨ Marisa Rackson, Chief of Staff, People at Notion 👋🏻 More about Notion: Startups move fast. That's why thousands of startups all around the world choose to build on Notion. In one place, you can organize, plan, and execute - whether you're managing investor outreach, documenting key decisions, or scaling operations. Apply now to get up to 6 months of Notion’s Business plan with Notion AI included, a $12,000 value. Ship quickly, stay aligned, and scale efficiently in one connected AI workspace. Learn more at https://ntn.so/cos-community. ​​​​​​​​​​​​​​👋🏻 More about Ask a Chief of Staff: ​​​​Ask a Chief of Staff is a premier executive search and career development platform dedicated to placing top-tier Chiefs of Staff and empowering professionals in strategic leadership roles. We serve ambitious professionals and high-growth companies by offering executive recruiting, mentorship programs, and career resources tailored to Chiefs of Staff. By addressing the lack of structured career paths for this role, we provide guidance, connections, and opportunities that accelerate leadership development and organizational success. ​​​​​Learn more at askachiefofstaff.com. TIMESTAMPS 00:00 Opening 01:59 Panel Introduction 05:51 What tools are absolutely essential in your day-to-day as a Chief of Staff? 10:28 Which AI-powered features have actually stuck in your workflow and which ones felt gimmicky? 16:55 How do you think about introducing tools/systems that support your principal and/or your team? 24:11 What AI tools or automations have you used that have really helped you in your day-to-day workflow? 28:36 What parts of a chief of staff role do you think should never be outsourced to AI? 37:45 Where do you foresee AI’s role growing in your org or adapting in your workflows? 43:14 Hot Takes 44:47 Q&A + Closing