315: Executive Decision Making and Why Every Leader Needs to Care About Customer Retention with Alisha Esmail

When a client goes quiet, most leaders assume everything is fine. Alisha Esmail would tell you silence is the clients exit ramp — because it's far easier to disappear quietly than to tell someone you're leaving. Alisha is the founder of Latch AI, an AI-native client retention engine, and her path to tech was anything but conventional: seven years in international development across Haiti, South Africa, Nepal, Jordan and Panama, followed by building an award-winning coffee company with direct supply chains across three countries and a micro-loan program supporting female-owned farms. In this episode, Alisha and Toni make the case that retention is not customer success's problem — it's a leadership problem that belongs to everyone. They get into what AI is genuinely doing to the retention landscape, why cutting CS teams has backfired badly for some companies, and the practical diagnostics any leader can run this week regardless of function. What we cover: Why every leader — engineering, product, sales, commercial — should care about retention How AI is reshaping the retention landscape, and "the war on clients" Bells and whistles vs boredom: when do customers actually leave a working product? No news is bad news — why silence is an exit ramp, not a sign of satisfaction The four-part retention framework: detect drift, score clients, run the safe play, capture the win Why "expansion ready" is the most missed category in most businesses Usage metrics: the data engineering leaders aren't capturing but should be and how it helps executive decision making   Useful Links Connect with today's guest, Alisha Esmail, on LinkedIn at https://www.linkedin.com/in/alisha-esmail/ and find out more about Latch AI at https://www.yourlatch.com. This episode was sponsored by our guest, Alisha Esmail. Thank you Alisha and Latch AI for helping to bring Leading Women in Tech to this community!