What we talked about
Join Dario de Santis as we delve into the transformative power of AI in reshaping how teams collaborate. Discover cutting-edge AI solutions that are breaking down barriers, enhancing communication, and fostering innovation across industries. From virtual assistants to intelligent project management tools, learn how AI is enabling seamless teamwork and driving productivity to new heights. Tune in to uncover how AI is not just a tool, but a game-changer in the world of collaboration.
Show notes
Dario de Santis watched colleagues at Cisco get seven back-to-back meetings booked in the same time slot and realized that AI-assisted calendar Tetris was solving exactly the wrong problem. Investing in optimization when a calendar is already overbooked just spreads conflicts onto evenings and weekends, the only real fix is fewer meetings, not better-arranged ones.
What we covered
- The insight behind Tweelin is deceptively simple: a workday has a hard ceiling of 8 one-hour or 16 half-hour slots, so no calendar optimization can increase productivity beyond that asymptote. Dario argues that the only way to increase resolution is to get people talking in the gaps between meetings, in five-minute bursts that currently require a week of scheduling overhead to arrange.
- Tweelin works by reading telemetry from users’ devices rather than just their calendars. Microphone and screen activity at the operating system level is a better proxy for real availability than calendar status, which is why someone can appear “free” on Outlook but be mid-conversation on WhatsApp. The system uses this cross-app signal to find a genuine available moment and then triggers the connection.
- The connection success rate of a standard phone call is around 12%. Tweelin achieves roughly 90% connection on the first attempt by waiting for the right moment rather than interrupting at a random one.
- Gartner named Tweelin a Cool Vendor in Digital Workplace Applications for 2024, one of only three companies worldwide in that category, without any external funding. Dario and his co-founders, all ex-Cisco and WebEx leaders, invested their own money and shipped a complete product before raising outside capital.
- He frames the problem historically: phone culture in the 1990s enabled fast, spontaneous collaboration, but the explosion of notification channels made interruptions feel rude. The response was to raise barriers, focus mode, asynchronous messaging, which solved the interruption problem but destroyed the spontaneous conversation that actually moves work forward.
- The next planned milestone is cross-platform bridging: a Slack user making a “wish” to talk to someone who uses Microsoft Teams, with the connection happening through whichever video tool makes sense. Dario also described a roadmap item where an LLM analyzes project context to identify who needs to talk to whom along the critical path, and proactively connects them before anyone realizes they’re blocking each other.
About Dario
Dario de Santis is the co-founder of Tweelin, an enterprise collaboration startup he built after more than 20 years in product and technical leadership roles at Cisco. He describes the pace of learning in four years of startup work as exceeding the learning from his previous 16 years in collaboration AI and product management combined.
- LinkedIn: https://www.linkedin.com/in/dariodesantis
- Website: https://tweelin.com
Episode 37 of the PreVetted Podcast.