AI Calendar Startup Blockit Raises $5M to Automate Scheduling
Tired of endless email threads just to schedule a 30-minute meeting? A new AI-powered startup called Blockit says it can handle your calendar negotiations for you—without you lifting a finger. Founded by former Sequoia Capital partner Kais Khimji and ex-Google Calendar engineer John Hahn, Blockit has raised a $5 million seed round led by none other than Sequoia itself. The company claims its AI agents can understand scheduling nuances better than any tool before it, promising a future where calendars “talk” to each other directly.
Unlike today’s dominant tools that rely on static availability links, Blockit is building what it calls an “AI social network for time”—a system where intelligent agents coordinate across users’ calendars in real time, mimicking human judgment while eliminating friction.
From Harvard Dorm Idea to Sequoia-Backed Reality
Kais Khimji first sketched out the concept behind Blockit nearly a decade ago as a Harvard student frustrated by the inefficiencies of coordinating group study sessions. After six years as a venture partner at Sequoia Capital—where he backed early-stage startups in fintech and AI—he decided it was finally time to become a founder himself.
“I’ve always believed that time is our most valuable non-renewable resource,” Khimji told us. “Yet we treat calendar coordination like a manual chore. That shouldn’t be the case in 2026.”
His co-founder, John Hahn, brings deep domain expertise: he previously worked on Timeful (acquired by Google), helped shape Google Calendar’s smart features, and contributed to Clockwise, another AI-driven scheduling tool. Together, they’re betting that large language models (LLMs) have matured enough to handle the subtle, context-rich negotiations that humans perform when arranging meetings.
Why Blockit Isn’t Just Another Calendly Clone
Most scheduling tools today—like Calendly or Microsoft Bookings—require one party to share a link showing their open slots. The other person picks a time, and if it doesn’t work, the cycle repeats. It’s efficient compared to old-school email ping-pong, but still rigid.
Blockit flips this model entirely. Instead of sharing links, users invite Blockit’s AI agent to represent them in scheduling conversations. These agents can:
- Interpret vague requests like “sometime next week in the afternoon”
- Negotiate trade-offs (“I’m free Tuesday at 3 PM or Thursday at 10 AM—which works better?”)
- Respect personal rules (e.g., “no meetings before 9 AM” or “buffer 15 minutes after calls”)
- Learn from past behavior to predict preferences
Critically, Blockit doesn’t just read calendars—it reasons about them. Using fine-tuned LLMs trained on millions of real-world scheduling interactions, its agents understand tone, urgency, and even cultural norms around time.
“Calendly automates the form-filling part of scheduling,” Khimji explains. “We’re automating the actual conversation.”
The Ghosts of Scheduling Startups Past—and Why Blockit Might Succeed
This isn’t the first time Silicon Valley has tried to kill calendar chaos with AI. Companies like Clara Labs and x.ai (founded by Sunil Nagaraj and Dennis Mortensen, respectively) made waves in the mid-2010s with AI assistants that booked meetings via email. Both eventually faded—Clara shut down in 2021, while x.ai’s domain was later acquired by Elon Musk’s xAI team.
So what’s different now?
According to Khimji, three things: better AI models, user readiness, and integration depth.
Today’s LLMs can parse ambiguous language and maintain context over multi-turn dialogues far more reliably than earlier systems. Meanwhile, professionals are drowning in coordination overhead—especially in hybrid work environments where time zones and focus blocks complicate planning. Finally, Blockit is designed from the ground up to integrate natively with Gmail, Outlook, and enterprise calendar systems, not just sit on top of them.
“We’re not asking users to change their workflow,” says Hahn. “We plug into the tools they already use and quietly take over the tedious parts.”
How Blockit’s “AI Social Network for Time” Actually Works
At its core, Blockit envisions a world where every user has a personal AI agent that manages their time. When two people need to meet, their agents communicate directly—checking availability, proposing options, and confirming details without human intervention.
Think of it like digital diplomats negotiating on your behalf.
The system respects privacy by design: agents only exchange necessary metadata (e.g., “available between 2–4 PM EST”), not full calendar contents. Users retain full control—they can override suggestions, set hard boundaries, or pause automation anytime.
Early beta testers report cutting scheduling time by up to 80%. One product lead at a San Francisco startup said she used to spend 5–7 hours a week coordinating meetings; with Blockit, it’s down to under 30 minutes.
Sequoia Bets Big—Again—on a Former Partner’s Vision
Sequoia Capital rarely leads seed rounds for companies founded by its own alumni—but when it does, it’s a strong signal. Pat Grady, Sequoia’s general partner and co-steward of the firm’s U.S. practice, wrote in a public post: “Blockit has a chance to become a $1Bn+ revenue business, and Kais will make sure it gets there.”
That confidence stems not just from Khimji’s track record as an investor, but from the market opportunity. The global scheduling software market is projected to exceed $5 billion by 2028, yet no player has truly solved the coordination problem—only the availability problem.
Blockit’s ambition goes beyond individual productivity. The founders see it as infrastructure for a more efficient knowledge economy. “If we can reclaim even 1% of the time professionals waste on scheduling,” Khimji says, “that’s millions of collective hours redirected toward creation, not coordination.”
What’s Next for Blockit?
The company plans to launch a public beta in Q2 2026, initially targeting tech teams, consultants, and executive assistants—groups that juggle complex, high-volume scheduling. Pricing hasn’t been finalized, but Khimji hints at a tiered model with free access for individuals and premium features for teams.
Long-term, Blockit could evolve into a broader “time OS”—a platform that doesn’t just schedule meetings but optimizes your entire day based on energy levels, deadlines, and priorities. Imagine your calendar proactively rescheduling low-priority calls when a project deadline looms, or suggesting focus blocks based on your historical productivity patterns.
For now, though, the mission is clear: end the era of “Does 2 PM work?” forever.
In a world overflowing with AI tools that promise efficiency but deliver gimmicks, Blockit stands out by tackling a universal pain point with genuine technical depth. Backed by one of the most respected VC firms in the world and built by veterans who’ve shaped modern calendar systems, it has the pedigree—and the product—to disrupt how we manage time.
If successful, Blockit won’t just save you from inbox clutter. It might give you back something far more precious: hours of your life.
