The Chief of Staff Podcast

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 https://www.chiefofstaff.network/.

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/

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/

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 https://chiefofstaff.network.

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

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

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

•

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.

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 https://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/

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

•

Trust is the deciding factor in landing a Chief of Staff role, and it compounds over years of working closely with a principal. Roughly five people from Eric's revenue forecasting team went on to become Chiefs of Staff because they already knew their leaders' businesses inside and out.

•

"Code is cheap now." When anything can be vibe-coded today and rebuilt tomorrow as the models improve, the bar for what is worth doing drops sharply, and the tedious monthly tasks a Chief of Staff used to grind through can be automated away.

•

AI is a productivity boost, not a compass. It cannot answer the value, mission, and purpose questions (where are we going, who are we serving, what matters), and handing those judgments to a model is a bad idea.

•

The five-month annual planning cycle is obsolete when the ecosystem can shift in five months. The more durable discipline is weekly: get clear on the purpose, decide what moves it forward this week, and define how you will measure progress.

•

Hard work is no longer the point. With AI moving faster than any top-down hierarchy can keep up with, everyone needs their own judgment about what is worth doing, and leaders create stability by being explicit about the mission, principles, and values that do not change.

•

A great flattening is underway, but there is no playbook yet, and stacking individual contribution, managing humans and agents, and strategic vision onto one person points toward more burnout. The Chief of Staff is well-positioned to be the brake on the system, asking whether the next bit of work is worth more than the team's long-term capacity.

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 https://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 doer trap is real. If you're great at executing, you'll be rewarded with more execution. Growth requires shifting from doing to orchestration, where one unit of your input produces outsized output across the org.

•

Chiefs of staff operate across altitudes (100,000-foot, 50,000-foot, and one-foot), and getting stuck at any single one is a warning sign. New chiefs of staff start in firefighting mode; the altitude mix should shift over time as governance and cadence get built.

•

Proactive gatekeeping is the opposite of bottlenecking. Think Amazon shipping manager, not roadblock. Sometimes you slow things down short-term so the executive engages at the right altitude with pre-aligned inputs, which speeds outcomes long-term.

•

Career stalls usually reflect a leverage problem, not a performance problem. High performers can be disincentivized from promotion because they're too valuable in their current seat. Counteroffers and external opportunities have unlocked internal moves in 24 to 48 hours.

•

Trust is the core output, built from three inputs: competence, integrity, and benevolence. Benevolence is not passivity; it can be "aggressively benevolent" pushback when others are misaligned with the broader vision. The strongest chiefs of staff are confidants, not yes-men.

•

Measure impact with an impact journal. Kirby keeps a OneNote annual tab where every deliverable, deck, and initiative is hyperlinked by date, making it easy to show concrete value during reviews and KPI updates when the work is otherwise hard to quantify.

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.

Guest: Tom Guthrie, President and Co-Founder, Chief of Staff Network

Nearly 100 chiefs of staff gathered in San Francisco, the epicenter of AI optimism and anxiety, to tackle the question: how do we lead transformation when adoption is uneven and the pace keeps accelerating? This episode recaps the first of seven global Chief of Staff Connect events in 2025, featuring workshops from OpenAI, Clarinet, Scribe, and LatchBio, plus surprising insights from cultural institutions managing dozens of board members and multiple unions. If you're navigating AI enablement or wondering how the role is evolving, this is your roadmap.

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

Episode Overview

Over 90% of chiefs of staff use AI every day. The harder question — how many are actually building with it — is what drove the agenda at Connect SF, the first of seven global Chief of Staff Connect events in 2025. Tom Guthrie breaks down what happened in the room, why AI adoption is so uneven across organizations, and what the shift from force multiplier to builder actually looks like when it's working.

About Tom Guthrie

Tom Guthrie is President and Co-Founder of the Chief of Staff Network, the global professional community connecting chiefs of staff across 20+ cities. He helped build COSN alongside Scott Amenta and now leads the network's programming, events, and community strategy. He hosted Connect SF in person and has a front-row view of how the role is evolving, at companies ranging from AI-native startups to century-old cultural institutions. He's one of the clearest thinkers in the community on what chiefs of staff can actually become.

Event Highlights

•

Connect SF drew approximately 100 chiefs of staff to San Francisco, COSN's biggest SF event yet, and the first of seven global stops planned for 2025

•

Laura Peng from OpenAI led a hands-on AI workflows workshop focused on what Codex now unlocks that wasn't possible before

•

Diane Sadowski-Joseph from Clarinet ran a session on enterprise AI enablement for mid-market and large companies navigating the transformation

•

The CTO and Chief of Staff from Scribe shared what it looks like to build AI-native products from the inside, and why the early builder days are the most fun

•

Jordan Ramsay and Alfredo Andere from LatchBio gave a rare inside look at a high-trust CEO and Chief of Staff partnership that's genuinely building something new together

•

Tom brought in chiefs of staff from the San Francisco Ballet and the San Francisco Symphony, each managing 50-80 board members and six or seven unions, as a deliberate reminder that the role's complexity runs far beyond tech

Key Takeaways

•

The AI adoption gap among chiefs of staff isn't about willingness. It's about whether the organization around them is ready to move. Companies built in the last 18-24 months are operating in a fundamentally different gear than those that aren't.

•

"Force multiplier to builder" is the defining shift of this moment in the role. It means moving from managing and improving what exists to creating something new, with AI as the primary instrument.

•

The fights on LinkedIn about what the Chief of Staff role actually is are a distraction. The real question is what the person in this seat can build right now, and whether they're asking it.

•

Fun is a leading indicator. The CEO and CoS relationships where there's genuine excitement about building, not just pressure to deploy, are the ones producing the most interesting outcomes. LatchBio's Jordan and Alfredo were a visible example.

•

It has never been a more valuable time to be a chief of staff. More complexity, more opportunity to build, and more leverage than the role has historically carried. The question is whether you're treating it that way.

Most Chiefs of Staff leave for a bigger title or more money. Lissa Sorgenfrei left to open a pottery studio. After eight years at German construction tech startup Capmo, where she moved from customer success to product management to Chief of Staff to go-to-market strategy, Lissa hit a wall. The problem wasn't burnout or bad leadership. It was realizing that the full-spectrum visibility she craved as CoS couldn't exist in any other traditional role. So she ran experiments, reduced to four days a week, and eventually traded spreadsheets for clay.

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

Guest: Lissa Sorgenfrei, Founder, Munich Clay Collective(former Chief of Staff at Capmo)

About Lissa Sorgenfrei

Lissa is the daughter of a Japanese mother and German father, raised in Germany with two cultural frameworks shaping how she sees the world. She studied business engineering with a focus on civil construction, originally dreaming of becoming an architect. She joined Capmo as one of the first employees during her studies, staying for eight years across multiple roles including functions in product, GTM and Chief of Staff. Now she runs Munich Clay Collective, a pottery studio in Munich designed around sensory experience and community.

Lessons Learned

The Chief of Staff role is inherently lonely, but not because you're isolated. You have full access to information across the company and behind closed doors, but you can't share most of it. You're trusted by employees and the CEO, but you're also filtering constantly. The only person who knows everything you know is yourself. That isolation is a feature of the role, not a bug.

Losing transparency after being CoS is harder than most people expect. Moving from a role where you knew everything the CEO knew to a narrower function, even one with leadership responsibility, feels like giving up "the sweet taste of nectar." Lissa struggled with this transition more than the actual work itself. If you've been CoS, prepare for that loss when you move on.

Good Chiefs of Staff make people feel seen. Lissa discovered her strength wasn't in process design or strategic planning, but in making employees feel valued and heard. This translated into motivation, retention, and culture sustainability as the company scaled. The interpersonal work isn't soft skills. It's leverage.

Being resourceful is a superpower, but it can also get in your way. Chiefs of Staff learn to solve undefined problems by finding the right people and dissecting challenges quickly. That same instinct can lead to over-optimization in areas where simplicity is better. Sometimes the best solution is just to drive 15 hours straight to Italy.

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

Guest: Marlen Heske, Chief of Staff at Enpal

Episode Overview

At fast-moving companies, the problem is rarely a lack of ideas or urgency. It's that everyone is chasing too many things at once. Marlen Heske, Chief of Staff at Enpal, has made it her job to slow that down just enough to create real clarity. In this episode, she breaks down her "clarity before harmony" philosophy, why saying yes to everything is one of the biggest failure modes in the CoS role, and how she's navigated 2.5 years at one of Germany's most ambitious energy companies.

About Marlen

Marlen studied socioeconomics at the University of Hamburg before discovering the Chief of Staff role during an internship at eBay in Silicon Valley. She moved through a deliberately varied career path including academic research, Greenpeace, an HR consultancy, an early-stage interior startup, and a circular economy venture builder before joining Enpal, where she serves as CoS to the Managing Director responsible for production engineering and supply chain.

Lessons Learned

•

Slow down before you execute. The first 90 days should be spent understanding the organization, the stakeholders, and the strategic direction before pushing anything forward.

•

Let go of perfectionism. The 80-20 rule matters. Not everything requires a perfect output, and chasing perfection will cost you more than the 20% you're trying to nail.

•

Balance patience with persistence. Choose your battles. Sometimes planting a quiet seed and watching it grow is more effective than pushing hard for immediate change.

•

Build real relationships. The role only works when people trust you enough to give you candid information. That trust is built through genuine human connection, not title or proximity to leadership.

Key Takeaways

•

The CoS role is one of the most flexible in any organization, shaped by company size, geography, seniority, and the specific gaps in the leadership team around you.

•

"Clarity before harmony" means making trade-offs visible, doing reality checks, and resisting the pressure to say yes to everything. Your job is not to keep the peace. It's to make sure the right decisions get made.

•

In Germany, the CoS role is still being adopted cautiously, with many companies using alternative titles. But adoption is accelerating, particularly in Berlin's startup ecosystem.

•

The CoS is not the decision-maker. The role is to bring transparency and surface trade-offs so that leadership can make better, faster decisions with a full picture.

How do you switch contexts between skincare operations, luxury recruiting, and B2B financial modeling all in the same day?

Zoe Jakubowich joins Chief of Staff Network Fellow, Tristan Lim, to break down the systems behind her fractional Chief of Staff practice, including her time-boxing method for client work, the daily exercise that prevents mental overload, and why she treats context switching like changing school subjects.

You'll learn the three essential skills every Chief of Staff needs (organization, hunger for ambiguity, emotional intelligence) and how to build a network-driven business that compounds value over time without hard selling.

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