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.

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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.