Being a Chief of Staff is isolating. It doesn't have to be.
A private community of 500+ Chiefs of Staff, swapping real tactics, playbooks, and talk that make the role easier to do and harder to leave.
Trusted by Chiefs of Staff at:
You don't have to figure
this role out alone.
Most Chiefs of Staff are the only one in their organization.
A room of peers changes that.
You're solving problems no one else even sees, holding everything together late into the night.
You translate between vision and execution, carrying more than anyone realizes.
There's no one to pressure-test a hard call with before you make it.
You want to level up, but you have no benchmark for what great looks like at your level.
Real guidance means hiring an executive coach or consultant on your own dime.
Peers in the same seat who get it without you explaining the backstory.
A place to gut-check decisions before they land on the CEO's desk.
Real benchmarks on comp, scope, and how others structure the role.
Playbooks, templates, and people who celebrate the wins your company never sees.
Access to mentors, executive coaches, and industry leaders who would otherwise cost thousands.
Peer masterminds for strategic growth.
Meet a few of your future peers.
Current Chiefs of Staff running point for CEOs at companies you'd recognize.
Sydney Falle
Chief of Staff at Lodestone People Consulting
Auriel Jones
Office of the CEO at
The Family Business Consulting Group, Inc.
Nikol Toteva
Fractional Chief of Staff
Josephine Chua
Chief of Staff at Onton
👉 Ready to find your people?
What's Inside
Mentor Network
Connect with veteran Chiefs of Staff who've navigated board dynamics, fundraising, and scale. Real advice from people who've sat where you sit.
Weekly Programming
Live workshops, expert AMAs, and tactical teardowns that keep you sharp.
Problem Solving Labs
Bring your hardest current challenge to a small-group lab and leave with a plan you can run on Monday.
First Look at Unlisted Roles
When you're ready for your next move, see Chief of Staff roles before they go public and get warm referrals from the community. No job-board grind.
1:1 Time with Clara
A strategic sounding board for the calls you can't take to anyone inside your own company, plus career coaching when you want it.
I built this because I needed it.
I spent years as a Chief of Staff at a fast-growing startup. I was the only person in the building with my title, holding everything together, with no one to compare notes with. Even on the best days, it was isolating.
So I built the room I wish I'd had. Today, Ask a Chief of Staff is a community of 500+ Chiefs of Staff trading the real playbooks, benchmarks, and advice that make the role easier to do and make you better at it.
If you're the only Chief of Staff in your company, you don't have to figure it out alone anymore.
Ex-Chief of Staff, Hugging Face
Tory Burch Foundation Fellow 2025
Inc. Female Founders 500
60K+ followers on LinkedIn
Clara Ma
CEO and Founder of Ask a Chief of Staff
However you arrive, there’s a place for you here.
Monthly Subscription
$99.99/month
no long-term contracts, cancel anytime.
Join a community of 550+ Chiefs of Staff
Get guidance from 50+ experienced
Chief of Staff mentors
Unlock 100+ templates, playbooks, and practical resources
Watch 150+ workshop recordings and expert sessions on demand
Book complimentary 1:1 Career Chats
with Clara Ma
Discover exclusive job opportunities
Attend member-only dinners, co-working days, and networking events
Participate in live workshops, coaching, and office hours
Get featured through speaking, writing, and publication opportunities
Limited Spots
Annual Subscription
$999.99/year
no long-term contracts, cancel anytime.
Everything in the Monthly Membership, unlocked for a full year
Save 15% with annual billing
Receive a limited edition swag bag
Early access to new resources and programs
Limited Spots
Josephine moved to SF as a first-time Chief of Staff.
Ask a Chief of Staff gave her a head start.
The Ask a Chief of Staff community has been amazing for me. When I moved to SF as a first-time Chief of Staff, I wasn’t really sure to expect. I had neither a footing in the role nor the city, and this community has provided both! I’ve met up with some wonderful people I now call friends, and have used the available resources to get better at what I do. I uses the 30-60-90 day plans as a framework to how I should be performing. I hope to be able to give back to this community as much as it has helped me!
Josephine Chua
Chief of Staff at Onton
Questions before you join?
🌎 Is this community only for US-based Chiefs of Staff?
🤝 How do members actually connect with one another?
🧩 Can I connect with members in my industry or company stage?
🎓 Do you offer mentorship or coaching?
🔎 Can you help me find my next Chief of Staff role?
📍 Do you host in-person events?
🎥 What if I can't attend a workshop live?
⏰ How much time do I need to get value from membership?
👀 Which membership plan is right for me?
📚 Can I use my professional development budget to pay for membership?
⛓️💥 Can I cancel my membership anytime?
