In this episode, Kyle Coleman shares how resilience shaped his career and why AI should accelerate execution, not dictate strategy. He offers practical examples of how sales and marketing teams can use AI to move faster, market the problem, and stay focused on what truly drives growth. Drawing from his experience at Looker and Clari, Kyle talks about how to build teams that trust each other, work efficiently, and stay aligned during change. He also reflects on parenting, staying present, and creating a work rhythm that keeps what matters most in focus.

• 00:00 Cold open: AI isn’t your strategy

• 00:27 Intro & Kyle’s background

• 02:11 Resilience from mom; embracing hard problems

• 04:03 Creativity, iteration, and no silver bullets in marketing

• 05:25 What ClickUp is: the converged workspace vision

• 07:28 ClickUp as SMB-friendly CRM & flexible platform

• 09:12 How AI changes campaigns & execution velocity

• 11:41 Don’t outsource strategy to AI; quality vs. volume

• 14:39 Sales: AI handles routine, humans connect strategy

• 16:08 Careers: be an AI native; show your POV and workflows

• 19:02 Process thinking: automate segments, save hours

• 20:26 Engineering gains; judgment still required

• 21:39 Weekly AI-use-case ritual; lead scoring example

• 24:18 Removing stigma around using AI

• 25:39 Culture: trust, autonomy, accountability, high standards

• 28:20 Decide with 80% info; iterate

• 28:49 Looker & Clari: market the problem, then the solution

• 32:12 Team stages; generalists → specialists

• 33:31 Hiring signals for curiosity

• 35:33 Performers vs. durable operators

• 37:07 Career advice: run toward the fire

• 39:59 Parenting, presence, and east-coast schedule

• 41:50 Close