Ari vs Sidekick Scheduling

Ari is an AI scheduling assistant that users CC on an email thread to find times that work for participants and arrange meetings. With permission, it reads Google Calendar and Microsoft 365 calendars and can create, update, or cancel events. It processes email content in threads where it is copied to identify scheduling requests. Listed services include Gmail, Outlook, Google Calendar, Microsoft 365, Zoom, Google Meet, and Microsoft Teams. Ari's Mac and iPhone apps can record and transcribe meetings, summarize them, and help book follow-ups; recording starts only when the user presses record. The macOS app keeps recordings and transcripts on the device unless cloud features are used. The Free plan allows 10 meetings total and one Google and one Microsoft calendar. Basic costs $24/mo, and Premium costs $39/mo. The maker says email content is sent to Anthropic’s Claude API for scheduling-intent processing and is not retained beyond what is needed to complete the request. Ari may misunderstand intent or suggest incorrect times, so users must review and confirm meetings.

Sidekick Scheduling helps coordinate meetings through scheduling pages, email requests, and calendar automation. It finds meeting times that work for Sidekick users and can send meeting requests to non-users for confirmation. Forwarding a meeting request email starts a process that checks availability, coordinates with the guest, and can book an available time. Sidekick can also create calendar events, send invitations, and send reminders before meetings. Personal and team scheduling pages let hosts set availability, meeting permissions, and preferences; guests can choose among in-person, video, or phone options when offered. Team Pages require a Superhero subscription, though invited team members can join for free by syncing their calendars. The free Hero plan includes one connected source and three scheduling pages, while scheduled meetings, groups, and contacts are unlimited. Superhero costs $5 a month and includes unlimited sources and calendars, unlimited scheduling pages, and Team Pages. Listed integrations include Gmail, Google Calendar, Outlook, Outlook Calendar, Thunderbird, Google Meet, Zoom, Teams, and Office 365. Sidekick is available on Android, iOS, and the web.