Oliv AI

Slack is where work goes to die. I keep hearing “Slack is where work happens,” but honestly, I’m not buying it. Yes, I agree, Slack does make starting a conversation quite effortless. Need to vent? It’s right there. Want to brainstorm? You’re one click away. But here’s what I’ve noticed: - Issues get raised but rarely make it to ClickUp (or wherever work is tracked). - You join a thread and suddenly end up in an entire channel—flooded with noise and distractions. The truth is, I really just wanted two types of communication: - Sync (like Gather) for real-time unblocking - Async (ClickUp) for tracking and collaborating on actual work Slack tries to combine both, and it doesn’t nail either. When it comes to getting things done, moving tasks forward, or keeping organizational knowledge accessible? That’s where Slack starts to fall apart. Conversations that start with real issues quickly devolve into complaint loops. People vent, share ideas, and express frustrations—but rarely do these discussions lead to real action. There’s no smooth handoff from a Slack thread to a ClickUp ticket or a documented solution. Instead, you end up with a lot of bitching and moaning while the actual work stalls. I’m starting to wonder if companies should cut Slack altogether. Not to save money or enforce a policy but to encourage more proactive problem-solving. What if we spent more time turning complaints into action items? Storing progress in a place everyone can access later instead of burying it in message chains? Ideas and insights are wasted if they sit lost in Slack. Because as easy as Slack makes it to talk, real work only happens if we turn talk into actions we can track and remember. What are your views on Slack? Does it help keep your work organized and accessible, or does it often get buried in conversations?

My sales playbook is basically a collection of "aha" moments from demo calls. I’ve done countless demos for Oliv, and each call reveals something new—a fresh perspective, a different use case, or a pain point I hadn’t considered. The real value is how customers link their problems to a feature of Oliv that could solve them, it gives me a chance to look at newer and fresher experiences that I can then repurpose in my future call. I’ve learned that when a product is at the core of someone’s workflow, they see it in ways that perfectly fit their process. The features become tools that tackle their pain points, allowing me to see Oliv with fresh eyes. It could be something simple, like fixing a coaching issue or how they struggle with bad data despite using multiple meeting recorders. Sometimes, these things that I’ve missed as a founder make these calls valuable. One of my favorite parts about Oliv’s Meeting Assist agent is how it pulls insights from these calls, showing us how prospects actually connect with the product—not just how we expect them to. It’s been a game changer in refining our pitch, shifting from “This is what Oliv does” to “This is how it can solve your exact problem.” Founders, how do you build your sales playbook? Do you draw mostly from customer feedback, or do you have other go-to sources? Let me know in the comments below.