In this episode, Luke Wallace, founder-turned-fractional growth leader and former Chief Growth Officer at Zipline Education, opens up about the moment high-visibility mistakes hit customers and forced him to rebuild his operating system. He shares the CEO feedback that drew a line between being nice and being kind, why he chose to hire an executive coach instead of switching jobs, and how he moved from heroic execution to scalable systems that don’t break under pressure.

Luke talks about over-communicating up and across with data, rebuilding trust after public misses, and setting binary outcomes that make expectations unambiguous. He also gets tactical on giving direct feedback without becoming a jerk, navigating team changes when a beloved generalist no longer fits the stage, running customer interviews to unlock stalled growth, and managing imposter syndrome as the stakes rise.

In this conversation, you’ll learn:

• How to turn painful, public mistakes into long-term fuel for resilience, credibility, and trust.
• How to use systems, documentation, and managing-up rituals to scale beyond “hero mode.”
• How to build a support loop (clear feedback, mentors, and customer interviews) to stay grounded and effective.

Things to listen for:

(00:00 ) Intro

(02:00 ) Luke’s early dream of becoming a pilot

(03:22 ) Into tech via school IT program

(05:00 ) Startup wins, scrappy realities

(09:15 ) Thank you to our sponsor, Navattic

(12:23 ) Direct feedback versus being nice

(23:54 ) Building a data-backed recommendation

(24:27 ) Handling high-stakes leadership talks

(25:01 ) Working through imposter syndrome

(27:19 ) Systems for scale over heroics

(30:19 ) Why Luke hired an executive coach

(34:42 ) The hardest conversations as a manager

(36:45 ) When the team and role evolve

(40:00 ) Giving clear, actionable feedback

(40:32 ) One-to-one coaching offer from Andrew

(43:20 ) Lessons learned from real failures

(44:26 ) Customer interviews as the unlock

(46:34 ) Key takeaways and ways to connect

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Luke: https://www.linkedin.com/in/lukewallace805/

Connect with Andrew:

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

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system