How to bring startup speed to big organizations episode artwork

EPISODE · Oct 21, 2025 · 39 MIN

How to bring startup speed to big organizations

from Executives Unplugged · host Keith Cowing

A startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust.Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if you move too quickly, you lose people. This episode dives into that tension. Atlassian’s Head of AI, Nisha Iyer, shares what happens when a startup founder joins a 10,000-person company and tries to build new AI products from the inside. She unpacks learning to slow down, earning trust, and building momentum the right way - without giving up the spark that made you effective in the first place.Executives and operators will relate to the tension between urgency and patience - and take away ideas for leading change without burning out your team or losing trust.00:00 — Moving fast meets resistance04:00 — “Learn the business”: slowing down to speed up09:00 — The big swing that fell flat — and the lesson in humility17:00 — Piloting change and earning trust one team at a time22:00 — Turning internal wins into customer-facing AI26:00 — Balancing empathy, momentum, and trust31:00 — Reducing fear, sparking excitement: leading through change36:00 — What’s next: voice tech, connection, and being more humanShoutouts: The First 90 Days — https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612 Atlassian — https://www.atlassian.com Rovo — https://www.atlassian.com/software/rovoFollow Nisha Iyer: https://www.linkedin.com/in/nisha-ranjani-iyer/Follow Keith Cowing: https://linkedin.com/in/keithcowing Subscribe to Keith’s free coaching via email: https://kc.coachSubscribe to the show: YouTube — https://www.youtube.com/@kcowing Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

A startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust.Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if you move too quickly, you lose people. This episode dives into that tension. Atlassian’s Head of AI, Nisha Iyer, shares what happens when a startup founder joins a 10,000-person company and tries to build new AI products from the inside. She unpacks learning to slow down, earning trust, and building momentum the right way - without giving up the spark that made you effective in the first place.Executives and operators will relate to the tension between urgency and patience - and take away ideas for leading change without burning out your team or losing trust.00:00 — Moving fast meets resistance04:00 — “Learn the business”: slowing down to speed up09:00 — The big swing that fell flat — and the lesson in humility17:00 — Piloting change and earning trust one team at a time22:00 — Turning internal wins into customer-facing AI26:00 — Balancing empathy, momentum, and trust31:00 — Reducing fear, sparking excitement: leading through change36:00 — What’s next: voice tech, connection, and being more humanShoutouts: The First 90 Days — https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612 Atlassian — https://www.atlassian.com Rovo — https://www.atlassian.com/software/rovoFollow Nisha Iyer: https://www.linkedin.com/in/nisha-ranjani-iyer/Follow Keith Cowing: https://linkedin.com/in/keithcowing Subscribe to Keith’s free coaching via email: https://kc.coachSubscribe to the show: YouTube — https://www.youtube.com/@kcowing Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

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How to bring startup speed to big organizations

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This episode was published on October 21, 2025.

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A startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust.Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if you move too quickly, you lose...

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