Ask a Chief of Staff: Where To Start When Your Boss Says: "Figure out AI"
🗓️ Join us on May 7th!
When your boss tells you to “figure out AI,” it can feel vague, overwhelming, and unclear where to even begin.
For Chiefs of Staff balancing competing priorities, complex stakeholders, and org-wide initiatives — the challenge isn’t just learning AI. It’s knowing what actually matters, what to prioritize, and how to make it useful without losing the human side of the work.
Join us for a practical session designed to help you move from “figure it out” to a clear, actionable plan — for both your own workflow and your organization.
✅ What you’ll leave with
Your personal time audit — where your hours actually go
A clear automation priority list — what to automate first
A 0–90 day implementation roadmap to get started
An ROI framework for pitching automation to leadership
A framework for evaluating AI tools across hiring, firing, and upskilling
A clearer career positioning strategy for the AI era
🙋 Who this is for
Chiefs of Staff navigating ambiguous expectations around AI
Chief of Staff professionals tasked with driving AI adoption across their org
Anyone trying to turn “figure out AI” into something concrete and actionable
🎟️ Please note, there will be a 100-person limit on this event. If you are unable to attend live, we will send a recording of the event afterwards.
🎙️ More about the Speaker
Katie Fortunato is the Co-founder and EVP of Platform Innovation and Strategy at Hire Innovations, a global leader in human-centered AI talent technologies. She drives innovation across their portfolio of brands, including—Recruitics, Talivity, and Jobstream—helping the world's largest brands modernize hiring while keeping people at the center.
In 2023, Katie launched Talivity, one of the fastest-growing communities for people leaders, and established the Innovation Lab. Her latest venture, Jobstream (2026), is a new affiliate category, and disrupting job discovery. Jobstream enables job discovery through social platforms with transparent creator monetization.
Before entrepreneurship, Katie built brand experiences for MTV, AOL, and The Wall Street Journal, where she established the publication's first brand experience with live video practice. Among other strategic growth partnerships developing ancillary revenue streams.
Katie serves as President of the Onward & Upward Foundation and sits on the Board of the American Red Cross Metro NY North Chapter. She splits her time between New York City and Greenwich, CT.
💜 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.