Jan. 28, 2025

The Hardest Decision of My Career: Inside Kieran Snyder’s CEO Journey

Show Notes
Guest Profile

This week, I talk with Kieran Snyder, the co-founder and former CEO of Textio, a groundbreaking company at the forefront of the AI revolution. Kieran’s journey is one of resilience, leadership, and innovation. We discuss how she transitioned from academia to leading a tech startup, raising more than $40 million in funding, and building equitable, high-performing teams along the way. Kieran opens up about the tough decision to step down as CEO after experiencing burnout and shares her path to recovery and rediscovery. We dive into her passion for building up young female leaders, from coaching girls’ basketball to supporting women in tech, and her talent for transforming surprising data into compelling stories through her newsletter, Nerd Processor. Whether you’re a leader, entrepreneur, or just curious about AI’s impact on the workplace, I hope this conversation will inspire and offer some practical insights as well. Let’s get to it!

In this episode:

(00:00) - Intro
(02:55) - Kieran's 8th grade science project
(05:07) - How parental influence shaped Kieran's career path
(08:29) - Academic journey in linguistics
(17:19) - Kieran's transition to tech
(23:47) - Founding Textio
(30:11) - Building a company with your spouse
(36:18) - Navigating product market fit
(46:46) - Burnout and stepping down as CEO
(56:35) - Leadership and knowing when to walk away
(01:01:23) - Detaching identity from career outcomes
(01:05:33) - How Kieran evaluates her performance as a CEO
(01:08:39) - The value of a board of advisors
(01:11:45) - Kieran's advice for someone recruiting a mentor, advisor or board member
(01:15:25) - Starting Nerd Processor and embracing creativity
(01:19:14) - How Kieran chooses what to write about
(01:23:20) - How to create substantial and insightful content
(01:30:11) - What Kieran has learned about hiring execs
(01:35:13) - Coaching youth basketball and personal fulfillment
(01:41:03) - Kieran's beautiful future
(01:42:59) - Who Kieran is becoming

Key Takeaways

Embrace Adaptability in Your Career Path: Kieran’s journey from academia to tech entrepreneurship highlights the value of being open to unexpected opportunities. Her move from linguistics research to building innovative software products shows that embracing change can lead to fulfilling and impactful career paths.
Success Comes from Hard Work and Resilience: The early challenges in building Textio illustrate that perseverance and iterative problem-solving are essential. Kieran shared how refining the product’s focus and pricing strategy transformed the company’s trajectory, emphasizing the importance of adapting to feedback and market demands.
Detach Self-Worth from Professional Outcomes: Kieran emphasized the necessity of separating personal identity from the success or failure of professional ventures. This mindset allows leaders to make decisions objectively for the company’s benefit without letting emotional attachment cloud judgment.
Startups Thrive on Customer-Centric Iteration: Kieran’s experiences underscore that startups succeed by staying close to customer needs. Her transition to focusing on enterprise clients at Textio demonstrates how listening to user feedback and evolving offerings accordingly can unlock new growth opportunities.
Collaboration and Complementary Skills Drive Leadership Success: The synergy between Kieran and her co-founder (and life partner), Jensen, demonstrates the power of complementary skill sets in a partnership. They shared values and aligned goals while leveraging their unique strengths to build and grow their company.

Quotes

“ I never intended to be a writer. I never intended to be an entrepreneur. And when we started Textio, I had just turned 40 and I had no intention of starting a company.” ~ Kieran Snyder

“The entire job before you have a product is to figure out what the product is you're building. Startups don't have [the advantages of larger companies]. So it makes you get really honest, really fast about whether you're building something that's actually useful to people.” ~ Kieran Snyder

“ Founders who outwork others are more successful. That's a fact. We can dress it up all we want, but the truth is you do have to be pretty obsessed with your business to get something off the ground.” ~ Kieran Snyder

“If you are not enjoying 80 to 85 percent of the way you are spending your working hours and you are lucky enough to have a choice, you should make a different choice.” ~ Kieran Snyder

“ I spent a lot of time doing the work that most founders struggle with, which is decoupling my sense of self-esteem from Textio's performance. It's very, very hard.” ~ Kieran Snyder

Links