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
