Jason Lemkin argues that 2021's outbound playbooks no longer work for startups. Generic AI-generated cold emails fail because they ignore context. He warns against hiring sales leaders stuck in old tactics and pitches SaaStr's AI Demo Stage, offering $500k to $5 million from Mayfield for the best AI-first pitch.
Chapters
You got to hire someone like him today. You can't hire the bitter CRO from 2021 that's complaining that outbound doesn't work anymore and doesn't have any solutions. I just see that left and right. Outbound doesn't work. Well, Kyle, it's working pretty good at Owner, but listen and learn how he does it. Okay. Yes. Look at this awful email I got from Slack the other day. I wrote this up on SaaStr. If you can read it, just the people are still running this old playbook. It's terrible. Reading from Slack in all caps. They're telling me it's a pioneering product for collaboration. Can we set up a 30-minute call? I'm given 2 time slots that are good for them. It doesn't say anything about me, nor do they know we're already paying customers. We're already paying customers for Slack and Salesforce. They don't even know it in their own CRM. This is literally a terrible AI droid. So we're still running this playbook. It maybe it works a little bit for Salesforce, for the mega brands, for the mega brands. We're just being in the game works at least a little bit. I don't think this works for startups anymore. So just I just wouldn't hire anybody who's all— who has no new ideas for their playbook or their ideas are going to bring in Clay. Okay, great. Amazing app. That's not going to do it in today's world though. It is working. Like the best ones are growing faster than ever, but it's not by running the old creaky playbooks. I'm just seeing them fail close to 100% of the time. So I think that's just about it. I'll highlight one more thing and then we can open it up to any questions. But we just announced if you're coming to SaaStr Annual, and you have an AI-first product or even an AI-first feature, apply to pitch it at the AI Demo Stage. Go on SaaStr Annual, there's a link, and you can come. The slots are super short. They're going to be like 2 minutes. Part of it's going to be for fundraising. Mayfield is going to invest in the number 1 pitch from $500,000 up to $5 million. So that's going to be fun. So there'll be a, there'll be a pitch part of it. If you have not raised money before, venture money, you're eligible to win for this pitch. But it's also just demos.
