Hi {{first_name|there}},
This week is about honest self-assessment.
Zoe Jakubowich on realizing she was her own worst enemy, and what she did about it. A community-wide AI survey to replace your gut feeling with actual data on where you stand. A generous gift from Brev (and a story about what early community support made possible). And, as always, the events bringing us together in person.
Scroll on!
A Fractional Chief of Staff’s Playbook
What if the path to sustainable work isn't finding the perfect job, but accepting you'll never be satisfied with just one?
Zoe Jakubowich spent years climbing through prestigious roles at Ernst & Young, Nordstrom's Trunk Club, Walmart's Jet Black, and a skincare startup she helped grow to acquisition. Each position taught her something new about strategy, operations, and building things from scratch. But they all taught her the same lesson about herself:
I'm the problem.
No matter the company size or role boundaries, she'd find things to do until she burned out.
Going fractional as a Chief of Staff was her solution to help her build necessary constraints. Now she runs five client projects simultaneously: skincare operations, food and beverage marketing, luxury recruiting, B2B marketing tech financial modeling, plus early-stage consumer investing. Her days are ruthlessly structured: 5am wake-up for heads-down client work, morning walk to reset, business development and events before lunch, client calls from 11am to 5pm. She time-boxes everything by looking one week ahead and preparing for specific conversations in advance.
The context-switching would overwhelm most people, but Zoe treats it like switching between school subjects; new folder, new focus. What makes it work is her daily exercise of writing what's occupying her mind in one column, then identifying one action to move it forward in another. It prevents anything from festering.
Perhaps most surprisingly, she's built this entire business without ever hard-selling. Every client came through existing relationships that naturally evolved into work because she follows through religiously on small commitments and adds value freely without expecting immediate returns. She learned early in her career that she'd "march off a cliff" executing tasks even after direction changed. Now she challenges thoughtfully, asking "why" before "how."
There is a tension she's still working through: How do you plan capacity when every project requires different cognitive energy at different times?
Her initial formula—one primary client, 2-3 projects, 10 hours for business development—proved completely impractical in practice. She's learning what resilience actually requires, one "Tetris combination" at a time.
Listen to the full episode to hear more about how Zoe runs her fractional CoS practice.
A thank-you to the CoS Network — and a small gift
Dear CoS Network community,
I'm thrilled to share that Brev just announced our $3.3M pre-seed round — and before anything else, I wanted to say thank you.
Most AI today is doing execution work in a vacuum. Without your goals, metrics, and live progress in the context window, you get motion without alignment -- and that's the missing link in a lot of AI deployments right now. Brev exists to close that gap.
When we launched our first product last May, this community leaned in early. You gave us feedback, took our calls, and trusted a young startup with real problems worth solving.
As a small thank-you, every organization from the CoS Network gets $100 in free AI credits when you sign up here: https://get.brev.io/CoS-Network
If you'd like to help amplify the launch, we’d be grateful! Featured here: LINK
Truly, thank you. We wouldn't be here without you.
With gratitude, Chris Pitchford Co-founder & CEO, Brev
🔮 Everyone thinks they're behind on AI.
Your peers think the same thing about themselves.
So who's actually ahead?
We're running a pulse survey on how Chiefs of Staff are adopting AI inside their organizations, what's working, what's stalling, and where the real benchmarks sit. The data goes straight into a community report you'll get back, so you can finally stop guessing where you stand.
Anonymous. 2-3 minutes.
📆 Upcoming Events
This Week
Chicago Chief of Staff Meetup — Wed, Apr 22
Connect with fellow Chiefs of Staff in Chicago for an evening of conversation and community building.
Next Week & Beyond
Chief of Staff London Mixer — Tue, Apr 28
Join the London CoS community for networking and discussion.
Detroit CoS Meet Up — Wed, Apr 29
Building the Chief of Staff community in Detroit — come meet your peers.
What Claude Cowork Actually Changes (CoS x Clarinet) — Thu, Apr 30
A practical look at how AI tools are reshaping the way Chiefs of Staff work, in collaboration with Clarinet.
May Events
Chief of Staff Launchpad (May-June) — Tue, May 5
A comprehensive program designed to accelerate your Chief of Staff career in the first 100 days and expand your leadership well beyond.
Boston CoS Meetup — Wed, May 6
Connect with the Boston CoS community over coffee and conversation.
Berlin Chief of Staff Meetup — Thu, May 7
Join Chiefs of Staff in Berlin for an evening of networking and show-and-tell.
The CoS AI Build-A-Thon — Thu, May 7
Roll up your sleeves and build AI solutions alongside other Chiefs of Staff.
Amsterdam CoS Borrel — Wed, May 13
A casual and show-and-tell experience for Chiefs of Staff in Amsterdam.
CoS San Diego Meetup — Thu, May 14
Building the San Diego CoS community — join us for an evening meetup.
Chief of Staff Connect - San Francisco — Fri, May 15
A forum for San Francisco-based Chiefs of Staff to connect and share insights.
AI & The Law: An Operator's Guide to AI Risk, Governance, & Contracts — Tue, May 19
Navigate the legal landscape of AI with practical guidance on risk management, governance frameworks, and contract considerations.
Building an AI Champions Program That Actually Works — Thu, May 28
Learn how to create and scale an effective AI adoption program within your organization.
June Events
Chief of Staff Connect - Austin Forum — Thu, Jun 4
Join the Austin CoS community for structured discussion and networking.
Chief of AI Fellowship — Thu, Jun 4
An immersive program for Chiefs of Staff leading AI initiatives at their organizations.
best,
Scott
Founder, Chief of Staff Network & BizOps Network