The Hire Most Founders Make Too Late | Kate Connolly, KaaS

Feb 19, 2026

48:14

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Investors don't invest in you to be a very expensive administrator. So why are you still managing your own calendar at Series A?

In this conversation on Follow the Gradient, Kate Connolly, founder of KaaS and former Chief of Staff at DeepMind, breaks down why most founders wait too long to get executive support and what it costs them when they do.

This is not a conversation about hiring an assistant. It is about how operational leverage changes the speed of every decision a founder makes, from fundraising to hiring to product.

We talk about:

Why you cannot solve the strategy problem before you solve the operational problem
The concrete difference between an EA and a chief of staff, and which one you actually need first
What VCs privately tell Kate about founders who refuse to delegate
How a 60-minute calendar audit can reveal where your week is leaking
Why the most common chief of staff hires fail within months due to role scoping
What great EAs do before they are asked, and how to interview for that instinct

This is not a playbook for outsourcing tasks. It is a conversation about what changes in a company when the founder stops being the bottleneck, and what it takes to get out of your own way.

Our biggest takeaways, including Kate's view on where founders misjudge their own leverage:

https://www.followthegradient.io/p/kate-connolly-podcast

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Where to find Kate Connolly:

LinkedIn: https://www.linkedin.com/in/kateconnollylondon/

Website: https://withkaas.com

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🎙 Follow the Gradient: conversations about building a business from Europe while staying sane.

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