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Clockwise Gave Meetings a Curfew - Then Time Ran Out
The calendar assistant moved 23 million meetings and made 8 million hours of room for deep work. Now that its team has joined Salesforce and the service is gone, its best ideas - and its sharpest limits - are worth a proper postmortem.
The AI Planner for People Who Don’t Trust AI Planners
Trevor AI turns the wishful thinking of a to-do list into appointments with yourself. Its defining feature may be the restraint to ask before moving anything.
The Most Valuable Person in the Room May Be the One Who Made the Room Work
Cara Boniecki built a career in the machinery behind executive decisions - then began teaching that machinery to everyone else.
Blockit AI
Blockit AI is a San Francisco startup building an AI scheduling agent that runs your calendar for you. You cc it on an email or ping it in Slack, and it books, reschedules, and negotiates meetings autonomously - learning which meetings are movable and which are not. When two Blockit users need to meet, their agents talk to each other directly, skipping the human back-and-forth. Founded by former Sequoia partner Kais Khimji and calendar veteran John Han, the company raised a $5M seed round led by Sequoia in January 2026 and says it has coordinated more than 100,000 meetings across 200+ companies.
Prachi Gupta
Prachi Gupta is VP of Engineering at Google, leading the Workspace Communication & Time Management portfolio - Gmail, Chat, Calendar, and Tasks - for hundreds of millions of users worldwide. A graduate of IIT Roorkee and Ohio State University, she spent over eight years as VP of Engineering at YouTube before moving to Workspace, where she now sits at the intersection of Google's AI transformation and its most-used productivity tools. Her current mandate: turning Gmail into a Gemini-powered personal proactive assistant.