Host: Tristan Lim, Chief of Staff Network Fellow and Founder, Beyond Founders

Guest: BreeAnne Yek, Chief of Staff, Series A MedTech and luxury wellness startup

Episode Overview

Almost every piece of advice given to Chiefs of Staff points outward. Manage the principal, manage the team, run the process. BreeAnne Yek's argument is that none of it works until you can manage the one system you actually control, which is yourself.

She and Tristan Lim get into behavioral design as a core Chief of Staff skill, the difference between someone's intent and their skill, and what to do when a working relationship breaks past the point of repair.

About BreeAnne Yek

Bree started in Singapore's public sector at the Attorney-General's office, in knowledge management and training and development. Watching an enterprise system fail on contact with actual human behavior is where her people-before-process philosophy comes from. The system had been designed three years before she arrived, and the people who built it understood the workflow but not the humans running it.

She was headhunted into business development for oil and gas services, found she liked the revenue side of a business, and left in 2019 to build in climate. Her last startup was a Kickstarter-style platform that let people fractionally lend to climate projects, so the nonprofits and SMEs behind them could move off philanthropic capital toward something sustainable.

She's unusually direct about the two things she got wrong by the time that startup ended. She's now Chief of Staff to a Brazilian founder at a Series A, SF-based startup with a clinical device aimed at sports recovery and athletic performance. She works from Singapore.

Key Takeaways

- Understand how people already behave before you try to change anything. A process that makes sense on paper and falls apart in practice usually failed at the human layer, not the design layer.

- Assume good intent, then check for a skills gap. Most breakdowns with a principal aren't malice. They're communication, and communication is a skill that can be refined.

- Skill includes bandwidth. When someone overcommits, it's usually an honest misread of their own time and emotional capacity, not a broken promise. The same applies to you, which is the point.

- The best influence doesn't look like influence. Reflect the question back, let people work through their own thinking, then nudge the outcome slightly left or right. Asking directly for what you want rarely gets it.

- Ask whether it will kill the company in the next half hour. If not, drop the cortisol. But know which moments (fundraising, investor interest, user acquisition) genuinely can't wait, and move fast on those.

- Sometimes the repair is leaving. If you've honestly asked whether you adapted hard enough and you're still holding back the mission, someone else should take the seat.

Bree and Tristan met at a Chief of Staff Network event in Singapore earlier this year. This episode also picks up on Tristan's essay on life after being a Chief of Staff: https://www.chiefofstaff.network/blog/life-after-being-a-chief-of-staff

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Join us in Singapore at Chief of Staff Connect Singapore Forum

Guests: Tyler Denk, Co-founder & CEO, beehiiv | Brian Schneider, Chief of Staff, beehiiv
Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Most conversations about the Chief of Staff role happen with only one side of the table in the room. This one has both. Tyler Denk has never viewed any of his three Chiefs of Staff as an assistant, and the bar he holds Brian Schneider to is specific: carry enough context to sub into any meeting Tyler is running and make any call he'd make if he isn't there. What follows is a working picture of that model, including what happens to the job when the CEO shares the board deck company-wide and there's nothing left to translate.

About Tyler Denk

Tyler joined Morning Brew as employee number two in 2017 and built most of the infrastructure behind it, the content management system, the ad platform, the growth mechanics, carrying the newsletter from 100,000 subscribers to four million before the Insider acquisition. The thousands of weekly reader replies asking how it all worked convinced him the gap in the market was the tooling itself, not another newsletter. After a year at YouTube he co-founded beehiiv, first pitched as Morning Brew in a box and now an all-in-one platform for newsletters, podcasts, websites and communities. He runs the company with unusual transparency, publishing revenue, costs and the ten things keeping him up at night to the whole team every quarter, and writes Big Desk Energy, a newsletter that started with no strategy behind it and produced one of beehiiv's largest enterprise deals.

About Brian Schneider

Brian's path started as a Morning Brew college ambassador at UConn, where he pulled a thousand referrals a semester by walking into lecture halls with a pen and paper. He was working nine to five at Prudential at the time and spending his evenings at the Morning Brew WeWork before he had a job there, which is what got Tyler to bet on him for a sales seat he had no background for. He climbed from sales into revenue strategy over five years, then followed Tyler to beehiiv into a rev ops role while the Chief of Staff seat was already filled. He did that work for three years and moved into the seat when it opened, which is a longer game than most people in this role are willing to play.

Key Takeaways

COSN runs this podcast and its newsletters on beehiiv. If you're in the role now, PRO membership is where Chiefs of Staff operating at this level connect, and if you're working toward your first seat, the Chief of Staff Launchpad is the on-ramp.

Guest: Zen Foo, Chief of Staff, Aspire

Host: Tristan Lim, founder of Beyond Founders and Chief of Staff Network Singapore chapter lead

Episode Overview

Most companies want AI adoption to happen and can't figure out who should drive it. Zen Foo makes the case that the Chief of Staff is the only person with the cross-functional context to pull it off, then walks through the three stages every company moves through, from hype to beautiful chaos to governance. The conversation turns candid on the harder parts of the job: people pleasing, likability versus respect, and protecting your principal's trust when the calls get tough.

About Zen Foo

Zen started his career trading Treasury bonds and interest rate swaps at HSBC in London. The pay was great and the work was intellectually sharp, but doing the same thing every day felt like Groundhog Day, so he left before the money got too good. He moved into tech at Monzo, realized what he actually loved was generalist, first-principles problem solving, and eventually landed at Aspire, where he now runs Chief of Staff and leads AI enablement for the whole company. He frames the role as the ultimate learning experience: two to three years of learning every part of a business before you specialize.

Key Takeaways

- The Chief of Staff is naturally incentivized to master AI because the job is constant context switching. Zen hasn't opened Word, Excel, or PowerPoint in six months because he works out of Claude and it holds his context for him.

- AI enablement is deeply cross-functional, which is exactly why it needs the Chief of Staff. The CEO or COO is usually too far removed to own org-wide governance, policy, and shared tooling.

- The hard part isn't deciding what to build, it's getting people to adopt it. Token quotas and mandates don't work. Getting one person to their magic moment does, and enough of those micro moments add up to a company-wide shift.

- Teach people to fish. Zen's AI Champions program seeds at least one excited person per team, equips them with advanced techniques, then lets them evangelize and build on their own.

- If you're stuck in the weeds, treat learning AI as an investment and block real hours (Zen did two a night for a month). Ask Claude to build you a 30-day program from zero. The tool is both the instruction manual and the tool.

- People pleasing is common among Chiefs of Staff, and Zen admits he hasn't solved it. His honest read: it's part of what got high achievers where they are, and some of it you just accept.

Zen and Tristan met at a Chief of Staff Network meetup in Singapore, one of the network's fastest-growing chapters. If you're doing this work in Asia, that's the room to be in.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Join us in Singapore at Chief of Staff Connect Singapore Forum

Episode Overview
Speed is the currency of the Chief of Staff role, but Carrie McMahon argues the way to sustain it is to slow down. A two-time Chief of Staff at one of the fastest-growing AI companies in San Francisco, she treats energy regulation as a performance strategy, not a wellness perk, and shows why a depleted operator makes worse decisions right when the team needs them most.

About Carrie McMahon
Carrie came up through go-to-market, not operations. She started in sales at Zendesk, then built the sales-development and product-led-growth functions at Coda (now Superhuman), ran enablement at Benevity, and served as Chief of Staff and head of RevOps at Productboard. She's now Chief of Staff at Horizon3.ai. The through line is cross-functional building in ambiguity, which is also what led her to teach breath work, yoga, and somatics to other strategic operators on the side.

Key Takeaways

Explore more of Carrie's Somatic Coaching and Corporate programs on her website here: https://www.groundandregulate.com/

Guest: Alex Craig, Chief of Staff at PortSwigger

Host: Scott Amenta, Founder, Chief of Staff Network

Most companies say they're adopting AI. PortSwigger actually did it, and the results weren't what anyone expected. Alex Craig breaks down how a bootstrapped cybersecurity company built a real AI culture from the ground up and why, for Chiefs of Staff, the hardest part isn't the technology. It's figuring out where human thinking has to show up in the work.

About Alex Craig

Alex didn't apply for a Chief of Staff role. He kept raising his hand for problems no one else owned, and eventually the title caught up to the job he was already doing. He works directly with Daf, PortSwigger's CEO and founder, at a bootstrapped cybersecurity company of roughly 200 people in northwest England. His core function is reading organizational decisions and correcting course toward how Daf would actually make them.

Key Takeaways

• The fastest AI adopters weren't the engineers. Kitchen and front-of-house staff embraced it first. Developers pushed back hardest, resistant to anything non-deterministic.

• AI eliminated the lower-stakes work that gives you room to breathe. Slide formatting, meeting prep, basic synthesis. What's left is only the complex decisions, all the time.

• The biggest emerging problem isn't bad AI output. It's employees forwarding AI-generated work they haven't read, pushing decisions upward with no personal thinking attached.

• The incognito-context test: if your manager could produce the same output in five minutes with no context about you, there's no "you" in the work.

• A personal AI system is only as useful as the training behind it. Alex spent months building one that reflects his actual views, reading habits, and listening history. The mental model is a new hire you develop over time, not a tool you pick up and put down.

Alex is publishing a full technical breakdown of his personal AI Chief of Staff system alongside this episode. Look for his blog post, "I'm a Chief of Staff. So I Built Myself One."

Guest: Kanika Choudhary, Chief of Staff, People IX

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Most companies are buying AI tools before they understand how their own company actually works, and Chiefs of Staff are getting handed the mess to fix. Kanika Choudhary argues that Chiefs of Staff are becoming the de facto owners of AI transformation by default, not by design, and the ones who succeed start with a map, not a purchase order. The companies that win do the unglamorous foundation work first.

About Kanika Choudhary

Kanika started her career in finance at PwC, burned out, pivoted to marketing, and relocated to Germany. She spent eight years as a first employee at early-stage startups before joining the BREAK Fellowship, a program that selects 200 women from 4,000 applicants to explore entrepreneurship in Spain. She came out of that experience and joined People IX, a conversation intelligence company that uses AI to interview entire organizations, cross-reference what employees say, and surface what's actually happening inside companies, as opposed to what leadership assumes is happening.

Key Takeaways

- Map before you buy. You cannot automate what you cannot see. Process documentation is not glamorous, but it is the only thing that makes any AI implementation stick.

- The "safest" first project is often the lowest-leverage one. Chiefs of Staff who default to low-risk AI projects to avoid failure end up losing credibility faster than if they had swung bigger and missed.

- Build an MVP before asking for permission. Scope the project, show leadership a bare-bones prototype, then execute. Approval is easier to get when the answer to "what will this look like?" is not a deck.

- Leadership almost never correctly understands how their company works. People IX has not once confirmed a leadership team's hypothesis after interviewing the full organization. The urgency to deploy AI is real; the self-awareness to do it well is rare.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Guest: Eric Nehrlich, Executive Leadership Coach and former Chief of Staff for Google Search Ads
Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

AI has collapsed the time between an idea and a working product, and every leader is racing not to be left behind. Eric Nehrlich makes the case that the tool can speed up the work but it cannot tell you what is worth doing, and that gap is exactly where the Chief of Staff becomes most valuable. The conversation covers why the five-month annual planning cycle is obsolete, why everyone now needs their own judgment, and how a Chief of Staff can protect an organization from burning itself out.

About Eric Nehrlich

Eric started as an engineer and spent a decade in startups before pivoting to the business side at Google, where he landed on the revenue forecasting team in the fall of 2008. Staring down anomalies in front of Larry, Sergey, and the leadership team through the Great Recession built the kind of trust that no interview process can manufacture. In 2012 one of his product partners asked him to come run the business as Chief of Staff for Google Search Ads, a role he held for over six years before becoming an executive leadership coach at Too Many Trees. He is also the author of "You Have a Choice: Beyond Hard Work to Meaningful Impact," which provides a transformational framework to help you redefine success when working harder isn’t working.

Key Takeaways

The Chief of Staff Network is where this conversation continues, through events, connections, and conversations with other chief of staff practitioners at every level. Find it at chiefofstaff.network.

Guest: Delong Lu, Chief of Staff, Proton

Host: Scott Amenta, Founder, Chief of Staff Network

Delong Lu has spent nearly a decade at Proton, the Swiss privacy company behind Proton Mail, growing from one of its earliest product managers into Chief of Staff, the "loose radical" on a ten-person management team. He joins Scott Amenta to talk about the hardest thing on his plate right now: how a company whose entire identity is user privacy moves fast on AI without breaking the promise that defines it.

Delong covers how Proton built its AI assistant Lumo on zero-knowledge encryption, why every line of AI-generated code still needs a human who can defend it, and why nothing ships without human oversight. His core lesson for any Chief of Staff leading an AI transformation: culture eats strategy for breakfast, so get clear on your values before you argue about tools.

About Delong Lu

Delong trained as an electrical engineer at ETH Zurich, added a business degree, and started his career in technology consulting and derivatives sales in London before deciding something was missing. He found Proton in 2017 after five cold emails (the last one finally got a reply from founder Andy) and joined as one of roughly 30 employees to help launch ProtonVPN. Over the next decade he cycled through Proton Mail, accounts and payments, and other business units as the company scaled past 600 people. That ground-level path through product is what made him the natural pick when Proton created its Chief of Staff role in 2022.

Key Takeaways

- The Chief of Staff role is often born from structure, not strategy. Proton organized into customer-facing business units, each with its own P&L, which optimized for shipping fast but thinned out the connective tissue between teams. When cross-coordination outgrew what the CEO and CTO could hold alone, the role had to exist.

- A senior Chief of Staff runs on autonomy, not a daily check-in. Delong meets his principal weekly and trades messages as needed. The mandate is "whatever it takes to hit our targets." That freedom is both liberating and confusing, and it only works because the CEO genuinely has his back.

- The most valuable move is closing the gap between vision and reality. When Delong noticed the CEO's AI vision did not match what teams were actually executing, he surfaced the disconnect and turned it into a work stream. Deciding what matters most is a skill he carried straight over from product management.

- AI transformation is a culture problem before it is a tools problem. "Culture eats strategy for breakfast." Proton's mission-driven people would walk before they would force AI at all costs, and that shared clarity resolves the circular debates about what data connects to what tool. For Chiefs of Staff at less principled organizations, the work starts with getting the executive team aligned on values, not picking software.

- The human stays accountable. Proton's policy is firm: engineers must understand and defend every line of code, nothing ships to production without human oversight, and no customer PII goes into third-party tools. The in-house assistant, Lumo, is the default.

Delong is part of the global Chief of Staff Network community. Links to connect with him are in the episode.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Guest: David Kirby, Author of "The Ultimate Chief of Staff Guide" (2025), Former Chief of Staff at Ford Motor Company
Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview
The same execution skills that get you into a chief of staff seat are often what keep you stuck there. David Kirby breaks down the doer trap, why high performers get disincentivized from promotion, and what it actually takes to move from task completion to orchestration.

About David Kirby
David's path to chief of staff was anything but linear. He went to law school in North Carolina expecting to practice as an attorney, bounced around the country, and eventually landed in Detroit, where he owned a grocery store before pivoting into advertising and then the automotive industry. He landed his first chief of staff role at Ford by taking a calculated risk in a one-on-one with a new incoming executive, asking directly for the job he wanted. He went on to earn an MBA, continued operating as a chief of staff for years, and recently moved into the utility industry.

Key Takeaways

The Chief of Staff Network is where this conversation continues, through events, connections, and conversations with other chief of staff practitioners at every level. Find it at chiefofstaff.network.

Guest: Judy Abad, Chief of Staff, CFOO, Freshworks

Host: Scott Amenta, Founder, Chief of Staff Network

Judy Abad has oscillated between Chief of Staff and functional leadership roles at some of tech's most iconic companies, including Facebook, Instagram, Slack, WhatsApp, and Freshworks. In this conversation, she unpacks the key differences between owning metrics as a functional leader versus synthesizing priorities as a Chief of Staff, and why both paths build the skills you need for the C-suite.

You'll learn how to build credibility by running toward the hardest problems, why you should stop asking for permission and start apologizing later, and how to evaluate Chief of Staff opportunities with pointed questions that reveal whether the role is set up for success.

Judy's advice: think in decades, but act now, and know when to walk away from losing hands.

Learn more about Chief of Staff Network's upcoming events, courses, and membership on our website: https://www.chiefofstaff.network/

About Judy Abad

Judy began her career in tech at Facebook when the company had around 500 employees, starting in sales before becoming one of the first Chiefs of Staff to the CRO. From there, she helped launch Instagram's first ad products, ran product marketing at Slack as employee 100, and led business product launches at WhatsApp. She's also been an early-stage startup operator and investor. Today she's Chief of Staff to the CFOO at Freshworks, where she focuses on connecting cross-functional work and driving execution at scale.

Key Takeaways

- The CoS role and functional leadership are not rungs on a ladder, they are different lenses. Functional leaders own a domain and make decisions with imperfect information. Chiefs of Staff synthesize across all domains and know when to escalate. Both skills compound into each other over time.

- "No one knows what they're doing" is not an excuse. It's permission. Stewart Butterfield told Judy this before a major enterprise launch at Slack, and the point was that the person closest to the work, the person who lives and breathes it every day, is exactly who should be making the call.

- P&L ownership and team size are proxies for seniority, not guarantees of it. What actually matters for getting to C-suite level: the ability to learn quickly, high EQ, intense curiosity, and a strong sense of ownership. Chiefs of Staff can build all of these without ever carrying a functional title.

- Career decisions are two-way doors. Almost every move is reversible. The pressure to find the perfect forever role before you make a change leads people to stay stuck. Meeting yourself where you are in this moment is not a compromise, it is a strategy.

- Know when to walk away from losing hands and when to double down on winning ones. Thinking in decades means you are not just optimizing for the next role. You are building toward what will still feel meaningful when you are mid-career or beyond.