#87 - Caitlyn Wells (Upwell Strategies)

Carrie Kerpen’s first acquisition started as an acquihire—but quickly became something much bigger. Once Caitlyn Wells and Upwell Strategies joined The Whisper Group, their operations work became a key part of helping founders prepare for exit. In this episode, Carrie and Caitlyn share how the deal came together, why the partnership created immediate value, and the bigger lesson: you are not only buying what exists today but investing in the people and shared future you can build together. This episode is sponsored by **The Whisper Group**, helping women founders navigate exit opportunities with clarity, strategy, and confidence. Learn more at www.wearethewhispergroup.com    2:40 - Caitlyn’s Background and the Start of Upwell Strategies 4:39 - How Caitlyn and Carrie Met 6:13 - Building Their Working Relationship 9:04 - Planning Systems for Maternity Leave 11:01 - Caitlyn’s Operations Advice for Founders 14:16 - How the Acquisition Came Together 17:13 - Navigating the Negotiation and Legal Process 18:56 - Scaling Operations at The Whisper Group 23:00 - What Caitlyn Wanted From the Deal 25:09 - Equity, Timing, and the Mental Load 28:36 - The Five-Year Vision for The Whisper Group