The cofounder of Kayak, Paul English, is returning to the productivity game with a scheduling play: Supercal, a free platform that aims to make booking meetings easy and erode Calendly’s lead. The pitch is simple — remove the friction from group coordination, make the experience email-first, and add a level of AI that actually does the busywork.
How Supercal’s email-native scheduling sets it apart
Supercal’s signature feature is group scheduling by email. You can CC Supercal’s AI on a thread, give it access to read the calendars of everyone who replied, and have it propose an available time that fits your collective schedules. When it finds an opening, it books the meeting and responds to the chain with details — no polls, no click-this-for-more-options back-and-forth.
The service can sync as many as six calendars so people can aggregate work, personal, side-project, or board schedules without hopping around between apps. It comes with eight meeting types — regular 15-, 30-, and 60-minute ones, as well as a VIP type that grants time to high-priority contacts for a little while.
There are social presets for breakfast, lunch, coffee, and dinner as well. And the team plans to eventually integrate those with restaurant reservations through OpenTable, turning “let’s meet for lunch” into “table booked at 12:30,” in one seamless experience. It completes the core with pre-meeting context forms, automatic time zone detection, reminders, and templates.
Supercal’s freemium model, early roadmap, and priorities
Supercal has launched as free software, with the company indicating planned premium features will not result in locking core scheduling behind a paywall. That philosophy makes Supercal an aggressive choice in a market where teams typically start paying for basics, then add routing or collaboration as they need it.
English’s playbook is a familiar one: grow rapidly, virally, and at the individual level to build something that is fast and useful before moving on to paid features for teams and enterprises. With productivity software’s ground-up adoption dynamics, free-to-start can serve as a powerful wedge against incumbents.
AI as a meeting copilot to improve how teams meet
More than booking, Supercal is targeting the nature of meetings themselves. The roadmap lists optional post-meeting analysis with transcripts (and input from meeting scrubs) on pacing, volume, and filler-word use before coaching users toward clearer delivery.
The company also wants to help teams determine which meetings should exist in the first place. More to come: Next features on deck will include indicators of decisions or action items being recorded, emphasizing recurring sessions that tend not to be well attended, and giving signal re: sunsetting low-performing rituals — an area many teams struggle with.
The timing is right: Harvard Business Review has charted the rise in the hours leadership meetings take up, to more than 20 per week, and Microsoft’s Work Trend Index has tracked a significant increase in digital meetings since work became hybrid. In that framework, automation that shaves down scheduling logistics and improves results from meetings is not just a nice-to-have — it’s a productivity lever.
Assessing the competitive landscape for scheduling tools
Calendly is still the best of the category, offering advanced routing, round-robin distribution, and deep integration with CRMs and conferencing tools — many of which are behind paywalls. Big platforms also hang on: Google Calendar for appointment scheduling, Microsoft Bookings for 365 users, Zoom’s scheduler, Doodle (for polls), and the likes of When2meet.
Supercal’s differentiator is that it’s email-native in flow. Instead of driving every contributor to a hosted link or poll, the assistant operates in-thread, where people are already working. If it can keep that simplicity and layer the integrations teams are used to — Google Workspace and Microsoft 365 admin controls, Zoom/Meet/Teams links, Slack notifications, CRM hooks — then it has a chance in the stack.
But enterprise adoption will depend on trust and compliance. Buyers will seek data minification practices, granular permissions, SOC 2 and ISO 27001 certifications, and clear controls over calendar access and retention. The email CC model is promising, but security guarantees will decide where Supercal ends up: a side tool or standard system.
What to watch next as Supercal expands features and reach
Supercal is currently live on the web, with the team looking into browser and email plugins for it, as well as iOS and Android apps. Look for integrations that minimize context switching, team features — shared pools and audit logs — and enterprise musts like SSO and role-based access.
English has experience — he turned Kayak into a category-defining travel search engine — and that makes this a credible challenge to an incumbent. If Supercal can keep its free tier generous, demonstrate that its AI truly makes people’s schedules more efficient, and naturally scale integrations without compromising privacy, Calendly could have a real competitor on its hands.