0:00
/

When Should You Hire a Chief of Staff? Goodword's CEO and Strategy & Ops Lead Explain

This episode is special.

With A Chief of Staff podcast, I try to share the latest Chief of Staff trends, insights, and stories for you.

And to date, this is a unique episode!

This episode is with Caroline Dell, Co-Founder and CEO of Goodword, AND Lara Kuhn, the Strategy & Ops Lead at Goodword.

Caroline has been a Chief of Staff before, and recently hired Lara Kuhn for an early-stage generalist role at Goodword. Lara has been a Chief of Staff twice before too.

As you can now tell, this episode is going to be incredible, right?

Here are three big ideas from the episode:

  1. Caroline recommends that venture-backed startups should look to hire a generalist as early as possible, even within the first five employees. However, if a company’s product is extremely technical in nature, her stance on this different.

  2. Caroline thinks that if a Founder would like someone to be able to think and work like them, then it could be a good time to hire a Chief of Staff.

  3. Caroline believes that a Principal (e.g. a CEO) should try to support their CoS’s career after their CoS role. Caroline experienced this and the benefits of it, as people she worked with before became financial investors into Goodword.

Enjoy this episode with Caroline and Lara!

Watch podcast video


🎧 A Chief of Staff with David Nebinski

  • 0:00: Intros & When to Hire a Generalist

  • 4:30: Why Caroline Hired Lara at Goodword

  • 8:15: The Importance of Having Career Conversations as a CoS, Mentorship & Long-Term Relationships

  • 14:00: How Caroline and Lara Figure Out What To Work On

  • 19:00: When to Hire CoS vs a Generalist

  • 24:15: Framing the Role to Founders & Former Founders as CoS

  • 28:15: AI, Early-Stage Generalists & Being AI-Curious

  • 36:15: CoS Careers, Founder Support & Interviewing Founders as a CoS


As a reminder, A Chief of Staff with David Nebinski is available to listen here, here, here, here, etc!


💼 Open NYC CoS and CoS-Like Roles

Job Board

That’s all I got for now. Thanks again to Caroline and Lara!

Check out Goodword too!

-David Nebinski who had an incredible time at last week’s A Chief of Staff Mixer, thanks again to Sheena Gohil and Jen Flores for partnering with me!

PS: when do you think a CEO should hire a Chief of Staff? Reply back and let me know. I am curious what you think!

PPS: make sure you follow @achiefofstaff on Instagram and A Chief of Staff Podcast on LinkedIn for bite-sized insights and updates!

Discussion about this video

User's avatar

Ready for more?