The Skyp Newsletter
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Insights, tips, and strategies for modern AI-powered outreach and sales automation
How one of the most respected founder CEOs in tech rebuilt his company around AI.
I get a lot of heat for piling onto the AI-eats-jobs meme and I’m fine with that. Because it does. Skyp has 3 people, technically 0 employees. Lots of AI. And we’re more productive than my previous company with 20+ at any given time.
But Skyp is new–we started it because we saw that opportunity, to build a lean company that produced a great product.
How do existing companies compete with that?
Yes, a lot of them have reduced headcount significantly. And replaced those roles with AI–several companies I advise have done this, and done it well. Obviously people are replacing rote sales work with AI–and we help with that!
But there’s a difference between cutting costs and hunkering down in a lousy M&A market and actually transforming your company. Sure, you can slash customer support from 50 people to maybe 5, but is that really transformational?
The real question is: If I were starting this today, what would I do differently?
For most founders of established companies, that question is uncomfortable enough that they don't ask it. They keep using channels that have worked in the past, even though they don’t work as well. They adopt AI for the proven use cases. Maybe experiment a bit, and prototype in it.
If you started over, your culture would likely be very different. You’d probably be agent first. Where everyone uses AI first, before even thinking about hiring a human.
You’d probably keep the team much leaner because they can be more productive and efficient. OpenAI shipped Codex, which is used by 5 million people every day, with a team of just 40.
But how do you get there? To be truly AI native you have to ask your employees to automate parts of their own jobs. Possibly their entire jobs.
Not everyone wants to do that.
Jason Smith, CEO of Klue, made this shift. He calls it the “refounding”. He dramatically changed his team size, put AI at the core of how all work gets done, and found that rocketship feeling you get at the beginning of your company’s journey.
I'm sitting down with him to hear how he did it. What worked, what didn’t work. To learn what it really takes to refound an established company in the AI era. Would love it if you can join us–I’m sure you’ll have questions that I’ll learn from.
Join Us this Thursday, June 11.

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