Herding Squirrels Ep 07
w Dave Walters
Former CTO: Hired, LaCalle Group, & Spafinder Wellness 365
In this engaging episode, we explore leadership through the lens of technical teams with Dave Walters, former CTO of Hired, Lacalle Group, and Spa Finder Wellness. With 13+ years at The Knot Worldwide (XO Group) and 20+ years as a volunteer firefighter, Dave brings unique perspectives on leading high-stakes teams. Using LEGO® Serious Play® methodology, Dave shares powerful insights on team alignment, staying calm under pressure, and nurturing collective success.
About Dave Walters
Dave Walters is the former CTO of Hired, Lacalle Group, and Spafinder Wellness, after spending 13 years at The Knot Worldwide (XO Group). He brings a strong track record in scaling platforms responsibly, operational rigor that supports both growth and margin, and de-risking complex technical initiatives. Beyond the boardroom, he's been a volunteer firefighter for over 20 years and thrives in high-stakes environments - whether it’s coordinating rope rescue teams, heading into burning structures, or setting the technical strategy to bring the business vision to life, he brings calm leadership where it counts most.
Find More Dave on LinkedIN
Episode Timeline
[00:00:00] - Introduction to Herding Squirrels podcast and guest Dave Walters
[00:00:55] - First LEGO build: Dave creates a baseball diamond model representing his life outside work
[00:03:02] - Discussion of Dave's baseball background as a catcher and how it shaped his leadership approach
[00:04:01] - Second LEGO build: Dave's best team experience, featuring color-coded pathways converging on a common goal
[00:06:56] - Exploration of team timing challenges and managing "FOMO" when teams join projects at different stages
[00:07:30] - Third LEGO build: Dave's worst team experience model showing misaligned paths and disconnected effort
[00:08:43] - Discussion of course correction and communication strategies when teams go off track
[00:10:01] - Analysis of why teams fail to align (lack of context, missing the "why," team dynamics)
[00:12:22] - Comparison of technical team leadership with other leadership contexts
[00:14:15] - How baseball and firefighting experiences influenced Dave's leadership philosophy
[00:17:16] - The importance of staying calm under pressure and maintaining perspective
[00:19:26] - Discussion of how remote work and technology shifts have impacted technical teams
[00:20:46] - Dave's thoughts on AI as a transformative force for engineering roles
[00:21:42] - Final LEGO build: Dave's advice for new technical leaders featuring a growth staircase with support structures
[00:24:32] - Dave's reflection on the LEGO building process and wrap-up
Key Themes Explored
Team Alignment: Creating clear pathways toward common goals despite different starting points
Calm Leadership: Bringing perspective from firefighting experience to business challenges
Continuous Growth: The importance of mentorship and evolution throughout leadership journeys
Course Correction: How to identify and address teams moving in the wrong direction
Technical Context: Bridging the gap between technical teams and business leadership
Adaptability: Embracing technological change and continuous evolution
Notable Quotes
"I think in the business world, all too often, we operate like a set of individuals... High-performing teams know when to stay in their lane, but also when to pick things up that are outside their lane because it's necessary for success."
"An individual success is meaningless if the company as a whole is failing."
"When you're having a rough day or facing a tough scenario in the business world... This is not life and death. It's important, but it's not life and death."
"If you dig in your heels and refuse to change, you're going to get left behind... You have to embrace that change."
"That mentor that maybe got you from a senior engineer to an engineering lead may not be the same mentor you're going to need when you're going from a VP of engineering to a CTO."
About Herding Squirrels
Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein. Through LEGO® Serious Play® methodology and engaging conversations, the podcast explores the nuances of effective teamwork, leadership, and collaboration in today's evolving workplace.
