Most founders would notice a kitchen fire. A slow leak in the basement is different. Everything looks fine for months, and by the time the water shows up the damage is already done. That is how Alisha Esmail describes client retention, and it is the reason she went from running a coffee company to building Latch AI, a tool that flags which clients are slipping before they leave. "It's like the leak in your basement. It's not a kitchen fire, it's not a dumpster fire, but your basement is filling with water." About This Episode Alisha's path into AI did not start with software. It started with a coffee company that worked directly with farmers around the world, building supply chains for female farmers and a microloan program to help them out of poverty. Running a physical product business across continents taught her where the manual work piles up, and that is where she started adding software, then agents, then AI, to buy her team's time back. The turning point was an email. At the dinner table with her family, she learned that her biggest client, half of her monthly recurring revenue, had decided to go in a different direction. She had to excuse herself from the table. That moment pushed her to become, in her words, a retention expert if she was going to build a successful company. She won that client back, and they are still a client today, but the lesson stuck: keeping a client is far cheaper and far easier than reselling them after they leave. Latch AI is the system that grew out of that lesson. It connects to the tools a business already uses, its CRM, calendar, payment system, and support tickets, and sorts every client into one of four categories: at risk, slipping, ready, or stable. Two of those are time-sensitive windows. The point is to catch someone while they are slipping, before they hit red, and to ask for the renewal or the referral at the moment the client is actually ready rather than when the business happens to need cash. Alisha also explains why she did not start with AI at all. The retention engine ran as a manual process first, then her team ran it, then automation, and only then AI. Throwing the kitchen sink at a model without a real problem and a real process is, in her view, the most common mistake people are making right now. Travis brings the revenue operations side of the same problem. Most CRMs are a mess: duplicate contacts, pipeline stages nobody defined the same way, stale deals, and historical data dragged over from two previous systems. Layer AI on top of that and it amplifies the mess. Alisha agrees without hesitation: the cleanup comes first. The conversation closes on a counterintuitive point from Travis. Companies often document why they lost a deal, but almost nobody documents why they won one, and the expectations set at the moment a client says yes are where a lot of churn is born. About Alisha Esmail Alisha Esmail is the founder of Latch AI. Her background is in international development, which led her to start a coffee company that worked directly with farmers, created streamlined supply chains for female farmers, and ran a microloan program. She went through a tech incubator and won funding to build a platform around those microloans before the pandemic put it on pause. Inside the coffee business she built an AI brain and agents to streamline the workflow, and a manual retention and client-intelligence system that eventually became Latch. Today she helps business owners keep their clients longer and grow through expansion revenue, working with an invite-only early adopter program of agencies, coaches, clinics, and other repeat-relationship businesses. Key Takeaways Retention is a leak, not a fire - Nobody ignores a fire. Slow client loss feels like nothing is wrong, which is exactly why founders notice it too late. Treat it as urgent before it is visible.Build the manual system before the AI - Alisha ran her retention process by hand, then handed it to her team, then automated it, and only then added AI. The model speeds up a process that already works; it does not invent one.Ask at the right time - Renewals, upsells, and referrals fail when they are asked for at the wrong moment, usually when the business needs revenue. Latch's "ready" category exists to find the moment the client is actually a cheerleader.A few points of retention move profit, not just revenue - Once hard costs are covered, retained revenue can have an outsized effect on profit. In one example Alisha shares, a company that believed it retained about 80 percent of its clients discovered the real number was closer to 60 percent.Clean the CRM first - Duplicate contacts, undefined pipeline stages, and stale deals are exactly the variables AI has to grab onto. Feeding it a mess only makes the mess faster.Document why you won - Closed-lost reasons are common. Closed-won reasons almost never are, and the gap between what a client expected at yes and what got delivered is where churn starts. Chapter Markers 00:00 - Cold open 00:22 - From Coffee to Code 05:33 - Don't Throw the Kitchen Sink at AI 08:06 - Inside Latch: Four Client Categories and Early Wins 14:49 - Messy CRMs: Cleanup Comes First 18:29 - Growing Flat: The Retention Self-Sabotage Trap 21:59 - The Real Cost of Churn 24:28 - The Dreaded Email 26:47 - Retention Is the Business's Job, Not the Client's 32:32 - The Latch Dashboard and Where to Find Alisha Resources & Links Mentioned Tools & platforms Latch AI (Alisha's company; currently invite-only with a wait list)HubSpotStripeIntercomClaude Code Books / podcasts referenced Obviously Awesome by April Dunford Other resources Alisha's churn scorecard: message her on LinkedIn with the word "churn" and she will send it Connect with Alisha Latch AI: https://yourlatch.com/LinkedIn: https://ca.linkedin.com/in/alisha-esmailInstagram: https://www.instagram.com/alishaesmail/Road Coffee: https://roadcoffeeco.com/ Connect with Travis Rainier RevOps: https://rainierdigital.comLinkedIn: https://www.linkedin.com/in/travisscott24Instagram: https://www.instagram.com/travis.revopsYouTube: https://www.youtube.com/@RainierRevOps If This Episode Resonated Alisha's warning about layering AI on messy data is the same problem we see in almost every CRM we open. If you are not sure whether your data, your process, and your team are ready for tools like Latch, the AI Readiness Scorecard is a quick way to find out where the leaks are:
