The Chief of Staff Podcast

By Chief of Staff NetworkBusiness Careers

The Chief of Staff Podcast episodes

October 21Chief of Staff to the CEO, or to the Business? with Ryan Kelly
Guest: Ryan Kelly, VP, Chief of Staff, Veremark
Host: Tristan Lim, founder of Beyond Founders and Chief of Staff Network Singapore chapter lead

Episode Overview

Every Chief of Staff gets pulled between the CEO's fires and the work that changes the business. Ryan Kelly, Veremark's first Chief of Staff, settles it with a monthly check on himself, because a CEO kept happy day to day won't be happy at the end of the quarter. He also walks through how he pitched the role into existence, earned his founder's trust in week one, and explained the job to a company that had never seen one.

About Ryan Kelly

Ryan started out as a welder, joined the JCB graduate scheme, then quit to study Mandarin in China. He moved into business operations at ITRS Financial Services in London, where he got his first taste of M&A, spent time at Skyscanner, and ran his own consultancy for three years before settling in Singapore. He met Veremark's CEO at a vendor event (and again at the gym), pitched him on the need for a Chief of Staff, and then won the role in an open process against more than 1,000 applicants. He now sits on the leadership team of the Series B workplace trust company, which has around 300 people working fully remote.

Key Takeaways
Frame a new Chief of Staff role around velocity, not repair. "Things are creaking" looks backward. Helping founders move at the speed they want is a value-creating pitch, the same reason revenue roles are easier to approve.
Front-load trust. Ryan spent his first month's trip asking his CEO 500+ questions, named his own blind spots, and asked to have dinner with the CEO's family. Seven months in, he has never had to justify the role.
Say what the role isn't. Ryan's town hall intro read out the questions people had been asking him ("What are you even here to do?") and answered them directly.
Listen for the quiet noise. Late laptops for new starters were too small for the CEO's radar but were straining HR. Mapping the whole process fixed it for good.
The job is negotiation between competing priorities, which is why Ryan argues it stays human: "Be a human Chief of Staff and you'll add more value."

Tristan and Ryan met at a Chief of Staff Network meetup in Singapore. Find your local chapter and upcoming events at chiefofstaff.network.
1 hr 2 min
October 14Why AI Can't Be a Chief of Staff with Sawyer Middeleer
Guest: Sawyer Middeleer, Founder, Revi Systems (former Chief of Staff, Aomni)

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Every company has bought the AI seats. Very few have changed how they work. Sawyer Middeleer argues the gap closes when someone maps how work actually gets done before automating it, and that the Chief of Staff is usually the person with the view to do it.

Scott and Sawyer get into building tools you'll throw away in twelve months, the difference between what AI can do and what it can do well, and why AI Chief of Staff products can triage an inbox but can't do the job.

About Sawyer Middeleer

Sawyer came up through strategy and ops at a large e-commerce company and BizOps at scaling startups. In 2023 he joined Aomni, an AI sales research startup, as its first employee and Chief of Staff, and stayed the only non-engineer through its pre-seed and seed rounds.

Because he was closest to customers, he ended up shipping front-end features to production with Claude Code, straight from customer conversations and reviewed by the engineering team. Today he runs Revi Systems, helping Chiefs of Staff and other operators bring AI into their organizations without drowning in slop.

Key Takeaways
It's easy to automate and hard to automate well. The five-cent bot replacing the five-dollar human fails when nobody captured the context and judgment that lived in the person's head.
Map the process and the value it creates before choosing a tool. Where AI output and human output look the same, use AI. Where the human has "that special something," keep the person.
Assume the way you work changes every six to twelve months. The value you deliver to customers is durable; the rhythm you use to deliver it isn't.
Every role is becoming engineering. Chiefs of Staff don't need to become engineers, but they need to think in systems, architecture and build-versus-buy tradeoffs.
AI should add capacity, not justify cuts. An account manager who goes from 10 accounts to 15 is a reason to grow faster.

Sawyer leads the "Building the AI Flywheel" workshop at Chief of Staff Connect New York, October 22 to 23. Connect with him on LinkedIn: https://www.linkedin.com/in/sawyer-middeleer

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/
50 min
October 07Who Owns Culture? Yorm Ackuaku Changed Her Mind
Guest: Yorm Ackuaku, Former Chief of Staff to the CMO, WeightWatchers

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Yorm Ackuaku came into this conversation ready to argue that Chiefs of Staff own culture, then changed her mind. Her answer: leaders own culture through the behavior people watch, and the Chief of Staff owns the operating rhythm that either reinforces it or quietly erodes it.

Scott and Yorm get into what happens to a team when the top keeps turning over, how three principles drafted at a leadership offsite turned into an all-hands so popular they had to turn people away, and how a Chief of Staff keeps their own footing while everyone else's anxiety lands on their desk.

About Yorm Ackuaku

Yorm has spent more than a decade as a Chief of Staff, most recently at WeightWatchers, where she supported four leaders across different mandates, including a brand new Chief Engagement Officer role that combined three organizations for the first time. She started in accounting as a CPA and came up through Deloitte's technology risk consulting group before business school.

Her first taste of the role came through a Citi leadership program meant to develop leaders for franchises outside the US. As the most junior person on a cross-functional tiger team in London, she was handpicked to support a senior leader, which led to business manager roles in Dubai and Johannesburg. Before WeightWatchers, she built operations for a 500-person global marketing team at Vista (formerly Vistaprint).

Key Takeaways
Leaders own culture. HR and people teams own the systems and policies. The Chief of Staff owns the operating rhythm that holds it together: consistent messages month to month, decisions that match what was said, and forums where questions actually get answered.
Culture rarely breaks all at once. It erodes through hundreds of small moments: quieter meetings, fewer people challenging ideas, more side conversations, less willingness to experiment. During leadership churn, certainty goes first, and people start optimizing for survival and for whoever holds the most influence that week.
You can't get strategic alignment from a team that doesn't trust each other yet. Yorm once saw culture work as a luxury during a restructuring until her first CMO showed her the culture work was the strategy. In her telling, an offsite set the direction, a weekly Slack ritual built the muscle, and a monthly all-hands spotlight gave it meaning.
The job is to create clarity. People going through transformation don't expect certainty; they expect honesty and transparency. Say out loud what you know to be true, what you don't know yet, and that you'll tell them when you do. It grounds the team, and it grounds you.

New in the seat? Skip the process overhaul and find where trust has broken. In one role Yorm held more than 100 conversations in her first 60 days, asking which meetings waste time, which decisions surprise people, and where people feel unheard. Process doesn't fix trust. Trust is what makes process work.

Yorm counts the Chief of Staff Network among the outside sounding boards that kept her grounded through repeated leadership turnover. Connect with her on LinkedIn at https://www.linkedin.com/in/yorm/

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/
40 min
September 30 Inside the Family Office: The Chief of Staff Role with Donald J Cunningham
Guest: Donald J Cunningham, Head of Family Office for a senior member of the Qatari royal family

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

When your principal has virtually unlimited resources, the answer to almost every request is yes. That makes the job less about getting things done and more about knowing when, and how, to push back. Donald J Cunningham explains how the Chief of Staff role works inside a single family office, where there's no institution to hide behind and no clean line between the portfolio and the principal's personal life.

About Donald J Cunningham

Donald spent the first half of his career in capital markets and lower mid-market M&A, then hit a crisis of confidence about where it was headed. Friends kept telling him he'd make a great "person behind the person," so one restless night at 2am he applied to an obscure Indeed listing, calling himself a "recovering investment banker" in the cover letter. That led to seven years at a well-known hedge fund founder's family office in New York. He now leads the family office for his fourth principal, splitting his time between London and New York.

Key Takeaways

- Privacy isn't secrecy. The best principals are discreet and humble, and the high hedges around family offices are intentional. Don't expect them to come down, even as the industry adds more governance.

- There's no room for ego. Family offices run lean, often inside or next to the principal's home. If a toilet overflows, it doesn't matter whether you're the CIO or the housekeeper. Good family offices test for this in the interview.

- Three tools for advising a principal who can say yes to anything: name the trade-off (yes, but at the expense of what?), use the rule of three (say "I think this is a bad idea" three times with reasons, then execute), and anchor to the long term with a family charter or investment policy.

- Interview the principal as much as they interview you. Ask about their values, what keeps them up at night, and what happens when things go wrong. Prestige means nothing if the fit doesn't work, and red flags in the interview rarely go away.

- Corporate Chiefs of Staff being pulled into an executive's personal affairs should read it as trust, not a demotion. After a liquidity event, it can be an opening to help stand up a private office.

- The career path is horizontal. There's no associate-to-VP ladder in a family office. The reward is exposure, variety, and more delegation as trust grows.

Join the Chief of Staff Network

The Chief of Staff Network is where this conversation continues, through events, connections, and conversations with Chiefs of Staff in corporate, public sector, and family office roles. Find it at chiefofstaff.network.
1 hr 10 min
September 23 What AI Policy Is Borrowing From Humanitarian Work with Anna Aden
Guest: Anna Aden, Chief of Staff, Asia Pacific at Tony Blair Institute for Global Change

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

The humanitarian sector spent decades working out how to serve the collective good without bending to partisan, commercial, or political interests. Anna Aden has worked on AI policy and AI safety, and she sees that same structure in the ethical guardrails tech companies are writing now, from OpenAI's mission to Anthropic's Claude Constitution.

Anna is Chief of Staff to the Managing Director for Asia Pacific at the Tony Blair Institute for Global Change. She got there by way of refugee camps in Myanmar, the Syria response, and aid programs she ran in the hundreds of millions of dollars. She joins Tristan Lim for a conversation that runs from that start to what the job actually looks like inside a global policy institute: setting priorities by working out which dependencies are load-bearing, what changes when HQ is in London and you're in Singapore taking calls at midnight, and why empathy is the skill she thinks the role runs on.

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
1 hr 1 min
September 02 Speaking Directly When No One Else Will with KJ of Bifrost AI
Guest: Kartikeya Jaiswal (KJ), Head of Strategy and Operations, Bifrost AI

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

Episode Overview

Almost everyone in a company has the privilege of not saying the hard thing. KJ's argument is that the Chief of Staff is the one role that gives that privilege up, because founders rarely hear an honest read from anyone else on the payroll.

Recorded at the Bifrost office in Singapore, this conversation covers six years in the CEO's office across two startups, what the role looks like when the company is building physical AI, and why the working agreement between a Chief of Staff and a founder needs a version update every few months.

About Kartikeya Jaiswal

Kartikeya Jaiswal, who goes by KJ, spent his early career in commodity trading, corporate finance, private equity, and investment banking, always pointed at technology, then moved into consulting on energy transition with large global enterprises. He crossed into startups in 2020 at The Parent, where the CEO's office role took the company from Series B to Series D across seven countries, 30 million users, and the acquisition of Line Messenger's Vietnam business.

He joined Bifrost AI at pre-seed in late 2021, before ChatGPT, when AI companies still read to most people as science projects. Four years later Bifrost has moved to Series A, tripled its team, and sells computer vision model training and robotics evaluation software into maritime, aerial, space, Earth observation, and defense.

Key Takeaways

- High agency is essential and compassion is table stakes. The differentiator is being able to speak respectfully, directly, and bluntly all at the same time, especially when nobody else in the room will.

- Ask your founder the question before you need it: if I ever disagree with you, what is the best way for me to do it? That single conversation gives you a platform to be honest without spending the relationship.

- Priorities drift silently. The year opens with X as the goal, and by month three the founder's instinct has moved to Y without an explicit conversation. Asking point blank what has changed, on a quarterly cadence, is the job.

- The role divides into roughly two halves: process that has to run like clockwork because it is the spine of the company, and reactive, opportunistic work driven by a conference, a customer, or a raise. When the second half eats the first, flag it up front and send your input async so the decision still gets made without you.

- AI pays off first on what is repeatable, on data enrichment, and on internal tools, including finance dashboards built for non-finance people. On go-to-market, KJ's line is that you need to plow the field but you can't spray and pray, and financials still need a human in the loop.

KJ is based in Singapore, where the Chief of Staff Network runs a growing Southeast Asia community.

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
1 hr
August 26 You Are the Product: Managing Yourself as a Chief of Staff
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
53 min
August 19A Second Brain, Not an Assistant: beehiiv's Chief of Staff Model
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
The split that matters isn't seniority, it's how the principal frames the job. Tyler puts his Chiefs of Staff in the "second CEO" bucket rather than the glorified EA bucket, and everything downstream, authority, context, delegation, follows from that single decision.
Deployability is the sharpest frame in the episode. Brian gets dropped into whichever part of the business needs him most, currently a six to eight week turnaround on the ad network team where he operates as if he's running it, then returns to the Chief of Staff seat when the next problem surfaces.
Radical transparency deletes a chunk of the traditional job. When anyone can see KPIs and rocks at any time, Brian doesn't spend his days interpreting what the CEO meant. He reiterates and clarifies instead, which frees him for the harder work.
Refusing a room is a red flag. Tyler has no patience for "I don't have engineering experience" or "I'm not interested in finance." The job isn't domain expertise, it's getting to the root problem and pulling the levers to fix it.
Trust gets built by showing up when you say you will. Brian's been at beehiiv three years and still treats relationship-building with team leads as the prerequisite to solving anything. It's also what killed the internal pushback beehiiv got for creating a role that reports to no one and moves through every team.
Fifteen minutes, five days a week, beats an hour on a Wednesday. Tyler calls Brian every weekday morning on his ten to fifteen minute drive to the gym to level-set priorities. Most Chief of Staff pairs settle for the weekly, and it's almost never enough.

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.
54 min
August 12 Why the Chief of Staff Should Own AI Adoption, with Zen Foo
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
54 min
August 05Why Slowing Down is a Chief of Staff Superpower
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
Energy management is four things, not one: your daily rhythm, matching tasks to your natural energy, building in micropauses, and how you wind down at night. Most burnout hides as a "leak" in one of them.
The Chief of Staff holds the container for the exec team. If you're spiraling, there's nowhere for everyone else to land.
When you're depleted, your prefrontal cortex stops optimizing. You get reactive and make fast calls without the analysis to back them.
"How are you feeling?" is a better opener for an exec 1:1 than "How's your week?" It reads state and lets you tailor the next 30 minutes.
Yoga isn't shapes on a mat. The goal is quieting the mental noise that keeps your nervous system in low-grade fight-or-flight, which is exactly the noise operators live in.
Start small and stay consistent: two breath-work techniques mid-day for four weeks, box breathing (inhale 4, hold 4, exhale 4, hold 4) at your desk. It's a practice, not a one-time fix.

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

About The Chief of Staff Podcast

From the publisher's feed

The Chief of Staff Podcast is hosted by Scott Amenta, Founder of the Chief of Staff Network — a global community of CoS with local chapters across 25+ cities. Every week, Scott sits down with Chiefs of Staff and senior operators to unpack the frameworks, hard lessons, and unwritten rules of one of the most consequential roles in business. This isn't an outsider's take on the role. It's the conversation happening inside the world's largest CoS community.