The Chief of Staff Podcast

Sarah Kislak spent nearly a decade at Box, progressing from an executive assistant in a rotational program to Chief of Staff for a 1,000-person engineering org, and ultimately into product management.
In this episode, Sarah shares what she learned by observing a Chief of Staff before stepping into the role herself, how she ran a team of seven while keeping alignment across recruiting, finance, comms, and strategy, and the hackathon moment that made her realize she wanted to build products.
She unpacks the differences between an operator and a PM mindset, explains why she chose to follow her talent rather than her passion, and offers practical advice for Chiefs of Staff who are PM-curious — including how to run small experiments this week to test the fit.
Learn more about the Chief of Staff Network membership, courses, and resources at chiefofstaff.network.

Have you ever wondered what it takes to manage the intricate dance of politics and business? Meet Nick Greif, a seasoned leader who has seamlessly maneuvered through both the public and private sectors as a Chief of Staff. We delve into the path charted by Nick, who transitioned from the Chief of Staff for an LA city council member to a pivotal role in the corporate world. Nick's journey is a masterclass in adaptability, strategic coalition building, and transformational leadership.
If you've ever wondered how government offices are surprisingly like startups or how the Chief of Staff role varies across sectors, this is the episode for you.

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

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.

Bryan Silverman joined Suzy (then CrowdTap) as an SDR and never left. Over nearly 11 years, he's moved from enterprise sales to Chief of Staff, to running a business unit, to his current role as COO.
In this episode, Bryan talks with Scott about the leap of faith that brought him into the Chief of Staff role, what it means to be "involved in everything but in charge of nothing," and how establishing operating cadences became one of his most lasting contributions. He shares hard-won lessons on people management, the transition from doing the work yourself to delegating with context, and why driving leverage, not just output, has been the common thread across every role he's held.
Bryan also gets candid about the glass ceiling many Chiefs of Staff face around P&L ownership and people management, and how AI is shifting the balance from execution to problem selection.
Learn more about the Chief of Staff Network membership, courses, and resources at https://www.chiefofstaff.network/.
Tune into Bryan Silverman's discussion with Tom Guthrie on driving AI Transformation on AI for Operators podcast.

Chief of Staff Connect is expanding to seven cities in 2026, our biggest year yet. We're meeting Chiefs of Staff at one of the most critical inflection points in the role.
In this episode, Scott Amenta and Tom Guthrie break down the strategy behind Connect 2026 and why this year's theme — FROM FORCE MULTIPLIER TO BUILDER — defines where the profession is heading.
You'll hear:
Why we're bringing flagship Connect events back to London, San Francisco, and New York and what's different this year
The story behind launching Chief of Staff Connect Forums in four new markets (tune in to find out where!)
What it means to shift from "force multiplier" to "builder" and why that matters for your career
How we designed this year's events to be more practical, hands-on, and regionally relevant
Why tickets (Flagship and Forum) include annual CoS Network PRO+ membership and what that unlocks
The best Chiefs of Staff aren't just amplifying their executives anymore, they're building systems, frameworks, and infrastructure that transform organizations. Connect 2026 is where you learn how to make that shift.
Registration is open now at chiefofstaffconnect.com. Early bird pricing ends soon. Don't wait.