After years of backing startups, former Sequoia Capital partner Kais Khimji is switching sides — and he’s doing it with an AI calendar negotiation startup designed to eliminate the endless back-and-forth of scheduling meetings.
The startup, called Blockit, uses AI agents that can negotiate directly with other people’s calendars, acting like a smart executive assistant that never sleeps. And in a strong show of confidence, Khimji’s former firm Sequoia led Blockit’s $5 million seed round.
“Blockit has the potential to become a billion-dollar revenue company,” Sequoia general partner Pat Grady wrote, signaling just how seriously the firm is taking this AI calendar negotiation startup.
After years of backing startups, former Sequoia Capital partner Kais Khimji is switching sides — and he’s doing it with an AI calendar negotiation startup designed to eliminate the endless back-and-forth of scheduling meetings.
The startup, called Blockit, uses AI agents that can negotiate directly with other people’s calendars, acting like a smart executive assistant that never sleeps. And in a strong show of confidence, Khimji’s former firm Sequoia led Blockit’s $5 million seed round.
“Blockit has the potential to become a billion-dollar revenue company,” Sequoia general partner Pat Grady wrote, signaling just how seriously the firm is taking this AI calendar negotiation startup.
Why Blockit Is Different From Calendly
Scheduling tools aren’t new. Calendly, for example, still dominates the category. But Khimji believes most tools stop short of true automation.
Instead of sending links and forcing people to pick slots manually, Blockit’s AI agents talk to each other. If two people need to meet, their agents negotiate behind the scenes — no emails, no links, no follow-ups.
“It’s always been strange that my calendar and your calendar can’t talk to each other,” Khimji said. “Blockit finally fixes that.”
This approach positions Blockit not just as a tool, but as an AI-powered time network.
How the AI Calendar Negotiation Startup Works
Users can summon Blockit’s AI agent by CC’ing it on an email or messaging it in Slack. From there, the agent handles everything:
- Negotiates meeting times
- Accounts for preferences like lunch breaks or focus hours
- Chooses locations or video calls
- Prioritizes requests based on tone and urgency
You can even train the AI to interpret context — for example, treating a formal “Best regards” email as higher priority than a casual “Cheers.”
Khimji says the experience feels less like software and more like having a personal executive assistant who understands your working style.
How the AI Calendar Negotiation Startup Works
Users can summon Blockit’s AI agent by CC’ing it on an email or messaging it in Slack. From there, the agent handles everything:
- Negotiates meeting times
- Accounts for preferences like lunch breaks or focus hours
- Chooses locations or video calls
- Prioritizes requests based on tone and urgency
You can even train the AI to interpret context — for example, treating a formal “Best regards” email as higher priority than a casual “Cheers.”
Khimji says the experience feels less like software and more like having a personal executive assistant who understands your working style.
Powered by Context, Not Just Automation
Blockit leans heavily into what investors call “context graphs” — AI systems that understand the why behind decisions, not just the rules.
By learning user behavior over time, this AI calendar negotiation startup adapts dynamically, making smarter scheduling choices with each interaction.
The Bigger Picture
As AI agents increasingly move from chat to action, scheduling feels like a perfect wedge use case. If Blockit succeeds, it won’t just save time — it could quietly reshape how professionals coordinate their days.
For Khimji, the move from investor to founder may be overdue. For everyone else drowning in calendar chaos, this AI calendar negotiation startup might be exactly what work needs next.