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

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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00:00 Introduction

02:30 When founder mode becomes the bottleneck

07:29 EA vs Chief of Staff: defining the roles clearly

11:24 The 15-person chief of staff trap

14:46 The cost of waiting too long: velocity

17:08 The 60-minute calendar audit

19:09 Building your EA into a second brain

26:37 What to look for when hiring an EA

32:41 When everything compounds: 12-24 months in

34:41 Working with C Levels

46:01 Rapid fire