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.
Topics & Chapters 


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

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