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.

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

Key Takeaways

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

Key Takeaways

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 chiefofstaff.network.

Stephania Greco takes us inside the Chief of Staff role at Bicycle Capital, a growth-stage VC fund, and reveals how it differs from startup CoS work. Instead of managing product roadmaps and cross-functional teams, VC Chiefs of Staff focus on fundraising strategy, investor relations, and building the firm's operating system with minimal headcount.

Stephania shares tactical lessons from building Bicycle's infrastructure using fractional consultants and AI tools, why she views ambiguity as "a space where value is created," and how her resilience as an immigrant shaped her founder's mindset. Perfect for CoS professionals curious about the VC world or anyone managing lean operations.

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

Priyanka Peeramsetty has been a Chief of Staff, a growth operator, a community builder, and is now Engineering Operations Director at Crunchyroll — and she'll tell you the one thing that underpins all of it: integrity.

In this episode, Executive Coach and Chief of Staff Fellow, Tristan Lim, sits down with Priyanka to hear her insights on what actually makes a great Chief of Staff. She breaks it down as a three-level pyramid, shares how she once predicted an attrition wave before anyone else saw it coming, and explains why the CoS role can feel existential if you're not doing it right.

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

Sarah Kislak spent nearly a decade at Box, progressing from an executive assistant in a rotational program to Chief of Staff for a 1,000-person engineering org, and ultimately into product management.

In this episode, Sarah shares what she learned by observing a Chief of Staff before stepping into the role herself, how she ran a team of seven while keeping alignment across recruiting, finance, comms, and strategy, and the hackathon moment that made her realize she wanted to build products.

She unpacks the differences between an operator and a PM mindset, explains why she chose to follow her talent rather than her passion, and offers practical advice for Chiefs of Staff who are PM-curious — including how to run small experiments this week to test the fit.

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

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

If you've ever wondered how government offices are surprisingly like startups or how the Chief of Staff role varies across sectors, this is the episode for you.

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