Ask a Chief of Staff: From Full-Time to Fractional Chief of Staff
🗓️ Join us on September 17th!
The idea of stepping out on your own can feel exciting and overwhelming in equal measure. What does fractional work actually look like day-to-day? How do you position yourself when you've spent years as a full-time operator? And where do you even find your first client?
If those questions are top of mind, this session is for you.
Join us for a candid conversation with Shaina Anderson, former Chief of Staff at Yelp and founder of Hello Generalist and Manual Override — two businesses built to help tech leaders make the leap into independent work. She's navigated the transition herself and has spent years helping others do the same. No theory, no fluff — just real talk about what it takes to go fractional and actually make it work.
💡 What will attendees leave with?
A clear understanding of what fractional work is — and what it isn't
A framework for how to position yourself in a crowded market
Practical first steps for landing your first fractional client
Honest perspective on what the leap actually looks and feels like
🎯 Who is this session for?
Full-time Chiefs of Staff who've been curious about going independent
CoS professionals actively considering or exploring the fractional path
Anyone in the early stages of building their fractional practice
✅ How should participants show up?
No prep needed — just bring your curiosity and your questions
🎙️ More about the Speaker
Shaina Anderson is the founder of Hello Generalist and Manual Override, on a mission to help tech leaders work for themselves. 3 years in, bootstrapped, millions paid to fractional operators: Hello Generalist is the marketplace startups use to hire proven fractional operations talent — and Manual Override is where those operators learn to build businesses of their own.
Before this chapter, she was Chief of Staff for Yelp Restaurants' 200-person org and built 7 teams at Chewse from seed funding through acquisition. Her work's been featured in The New York Times, Rolling Stone, TechCrunch, Food Network, and Food & Wine.
Before she got into tech, she helped open (and close) a food truck, spent time on farms, sailboats, and tour buses... not exactly the standard path. It all feeds what she cares about most: helping people take real risks to build meaningful work that fits lives.
💜 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.