Positioning Yourself as a Chief of Staff

Feb 25, 2026

Guest

Rahul Desai

Guest

Lauren Werner

Guest

Thomas Guthrie

Rahul Desai, ex-GM of the Chief of Staff Network who builds hiring tools. Lauren Werner, current CoS and Head of Growth who advises candidates. Thomas Guthrie, Network president and framework-builder. They discuss what principals actually filter for, how to position non-CoS experience honestly, tailored outreach that wins meetings, and a fast cover-letter test to see if a role fits.

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ADVICE

Translate Cross Functional Roles Into CoS Experience

Don't rely on the title; map cross-functional operator roles (strategy, ops, client services) to CoS responsibilities with concrete examples.
Lauren Werner: explain how you acted as strategic glue and the outcomes you drove across teams.

INSIGHT

Tie CoS Work To Commercial Outcomes

Chiefs of staff must tie their work to commercial outcomes, not just tasks or titles.
Rahul Desai: show how prepping board decks or running all-hands directly improved fundraising, retention, or profitability.

ADVICE

Develop The Five Tool CoS Profile

Build the five-tool profile: analytical horsepower, people skills, industry/stage fit, AI capability, and strong personal vibe with the principal.
Thomas Guthrie: use past training (consulting/banking) as one proxy for analytical rigor but balance with people skills.

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Positioning Yourself as a Chief of Staff

How do you stand out when thousands of people are applying for the same Chief of Staff role? And what if you've never held the title before?

In this episode, Scott Amenta sits down with Chief of Staff Network President, Thomas Guthrie, former GM, Rahul Desai, and Head of Growth, Lauren Werner to break down what it actually takes to land a Chief of Staff role in today's market. The team covers what principals are really looking for (hint: it goes far beyond "someone really smart"), how to position non-CoS experience without stretching the truth, and why the best candidates treat the interview as a two-way evaluation.

In this episode, you'll learn:

The five traits that make a standout CoS candidate, and why you need to check every box
How to tie your experience to commercial outcomes, even if you've never carried a revenue number
Why cold outreach to principals beats the resume pile almost every time, and how to do it well
The cover letter exercise that instantly reveals whether a role is the right fit
What questions to ask in the interview to protect yourself from the "tractor beam" of a great founder
How to use the CoS Leveling Framework to make sure you're interviewing at the right level
Whether the Chief of Staff role is even the right next step for you

Ready to go deeper?

Chief of Staff Fundamentals is our self-paced email course covering 15 lessons on everything from building your principal relationship to leveraging AI in the role.

Whether you're exploring the CoS path or in your first 100 days, Fundamentals gives you the playbook to hit the ground running. Enroll in Fundamentals

Chief of Staff Launchpad is our six-week cohort program for current and aspiring chiefs of staff who want hands-on coaching, live sessions with experienced CoS leaders, and a peer network to grow with. If you're serious about accelerating in the role, Launchpad is the next step. Join the next Launchpad cohort.

Chief of Staff Network

Learn more about the Chief of Staff Network membership, courses, and resources at chiefofstaff.network.