Kill the Meeting Chaos: How Tweenlin Uses AI to Free Your Calendar

Off the Grid, On the Record by Yarek Matacz

S02 E35
34:42
Episode notes

Sick of living in your calendar? Founder Dario De Santis (Tweenlin) breaks down how his team is cutting the meeting overload—turning endless 1:1s and “quick syncs” into fast, human conversations without scheduling gymnastics.

We dig into:

  • The real cost of meeting sprawl (and why remote work made it worse)
  • How Tweenlin’s AI deflects 1:1s and small-group meetings into on-the-fly conversations
  • What early pilots show: measurable productivity gains and “empty calendar” serenity
  • Selling true workflow change into 10k–100k-person enterprises
  • Why you don’t fail if you don’t give up: Dario’s 4-year founder journey from idea → Gartner “Cool Vendor”

If your team complains about meetings, send them this.

Guest: Dario De Santis — Founder & CEO, Tweenlin

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Keywords
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