AI for Chiefs of Staff: What's Actually Working

​Chiefs of Staff are in a unique position when it comes to AI. You’re expected to help your leadership team work out what it means for the company, drive adoption across the organisation, and figure out how to use it to increase your own leverage, all at the same time.

​We’ll get into the questions that are difficult to answer from the outside: which tools are worth the money, where adoption is really happening, what you tell your leadership, what you quietly do anyway, and where you think they’re getting it wrong. The market is noisy, the claims are inflated, and the honest version of this conversation rarely happens in public.

​This is a curated, off-the-record discussion for 8–10 Chiefs of Staff at seed and Series A companies. We’ll explore where AI is expanding what one person can do, where adoption stalls, what remains overhyped, and how Chiefs of Staff can shape the thinking above and around them rather than simply execute it.

​Most Chiefs of Staff at this stage are the only one in their company. This is the peer group you don’t have internally.

​Expect a practical, candid conversation over breakfast — not a panel, not a pitch, and definitely not the LinkedIn version of AI.

​​Running order

​8:30am - 9:00am
Arrivals, coffee and breakfast served

​9:00am - 9:15am
Welcome, introductions and framing

​9:15am - 10:30am
Roundtable discussion: what is actually working with AI for Chiefs of Staff?

​10:30am - 11:00am
Informal conversation over coffee

​​Your hosts

​Helena Horsburgh is an experienced Chief of Staff who has worked at Twilio and Personio, driving transformation programmes, business operations and culture initiatives. She began her career at Dropbox across Sales, Partnerships and Programme Management, followed by a stint at Stripe in Revenue Operations. She has led hands-on AI adoption and readiness programmes and understands the balance Chiefs of Staff must strike between setting expectations, enabling change and delivering tangible impact across an organisation.

​Huw Walters is the Founder of Experimental Technology, where he has spent the past year working hands-on with small and mid-sized businesses putting AI at the centre of their operations. He has worked in AI since 2018, including as a Staff AI Product Manager at Meta and as Head of Product at an AI start-up acquired by TikTok.