Introducing Clockwise AI:
A first-of-its-kind calendar experience powered by GPT.
Sign up for beta
Future of Work
The Best AI Assistants for Scheduling in 2024

The Best AI Assistants for Scheduling in 2024

Judy Tsuei
September 21, 2023
Updated on:

The Best AI Assistants for Scheduling in 2024
Photo by 

Ever find yourself wishing for a personal assistant during one of those impossibly busy weeks? We’ve been there. Thankfully, we’re living in a time when artificial intelligence can act as our personal calendar assistant, helping us do everything from book meetings to block time for tasks.

Don’t let the tedious work of calendar management have a monopoly over your time. Instead, choose scheduling software with built-in automation features, so you can finally feel great about your time management.

In this quick guide, you’ll learn:

  • What an AI scheduling assistant is and how it can help you in your day-to-day life
  • 5 AI scheduling tools we recommend checking out today

Let’s start!

Top features of AI scheduling assistant tools

Let’s go over the types of features you can expect in an AI scheduling assistant:

  • Integration with your favorite tools. Always consider if a tool plays nicely with the apps you already use. For an AI scheduling assistant, it helps to choose a tool that integrates with your calendar app (e.g. Google Calendar or Outlook) and your video conferencing tool (e.g. Zoom or Microsoft Teams). The more harmoniously your tools work together, the better your experience will be.
  • Smart scheduling for meetings. A great AI scheduling assistant minimizes the dreaded back-and-forth of scheduling a meeting. It can help team members coordinate across different time zones and (depending on the tool) make sure meetings take place at their most efficient times.
  • Smart scheduling for tasks. Some AI assistants can also find time for your work.
  • Re-scheduling. Cancellations and follow-up appointments can be a nightmare to reschedule. AI scheduling assistants help streamline the process with automation.

Top AI scheduling assistant tools


ai scheduler

Clockwise is a time orchestration platform that helps you design your ideal day. Clockwise finds the most efficient times for you and your teammates to meet while creating long interrupted blocks of Focus Time in your schedule. Plus, it works on top of Google Calendar, which means Google Calendar users don’t need to switch to a new calendar app to enjoy the benefits of Clockwise.

Key features:

  • Flexible meetings. Once a day, Clockwise will move the meetings you marked as flexible to their best times.
  • Focus Time. Clockwise creates more Focus Time in your schedule by rearranging your existing meetings to open up long blocks of free time, perfect for focused work.
  • With Clockwise AI, you can simply send scheduling requests directly to Clockwise via chat. Clockwise uses natural language processing to understand your request — then handles it for you!


It’s free to start using Clockwise — just sign up with your work Gmail account.

Reclaim AI

Reclaim AI is a smart scheduling automation app that finds the best time for your meetings, tasks, habits, and breaks. It’s a small business’s very organized best friend. This AI scheduling software offers a combination of calendar management and task integration. 

The tool's real-time availability checks rule out scheduling conflicts. To add to that, Reclaim AI understands the importance of collaboration within a team. They do their best to get rid of messy scheduling dilemmas. 

Key features:

  • It auto-schedules the best time for one-on-ones so you don’t spend time scheduling them.
  • It considers the time in your schedule for travel, flexible breaks, and personal appointments to avoid burning out.
  • Optimizes high-priority and flexible time links for the quickest way to schedule a meeting with your team and clients.
  • Integrates your tasks and status while you are connected to Google Calendar, Slack, and Zoom.


Lite: Free (forever)

  • Limited to 1 user
  • 2 connected calendar sync

Starter: $8/month

  • Up to 10 users
  • Unlimited habits

Business: $12/month

  • Up to 100 users
  • Unlimited scheduling links

Enterprise: $18/month

  • More than 100+ users
  • Company-wide status templates


Similarly to, Motion is an automation tool that intelligently plans your day, schedules your meetings, and creates a perfect to-do list. You can have conversations and chats with Motion’s AI assistant to resemble natural dialogues, as they understand and respond to human language nuances. This assistant will make the transition to a new software smooth and easy to use.

This feature will give you everything you need without feeling overwhelmed. This software helps you to visualize how much work and time was actually spent during the week. 

Key features:

  • The meeting assistant performs as your “personal” assistant and deals with scheduling and communicating with the participants.
  • The project management planning tool measures what was done and collaborates to build each team member a custom schedule.
  • It automates your to-do list, calendar, and habits into the most optimal schedule.
  • Notifies and warns you if a certain task won’t meet a target deadline.


Starting: 7-day free trial

Individual: $19/month

  • 1- click email assistant
  • Automated AI scheduling and planning

Team: $12/month

  • Collaborative projects and tasks
  • Automated planning for each team member


Calendly can create personalized scheduling links that recipients can use to choose convenient meeting times. Its reputation as an efficient and user-friendly scheduling tool precedes it. They are one of the pioneers of sending meeting calendar links.


This eliminates the back-and-forth email exchanges that lead to confusion and frustration. Calendly integrates with almost all popular calendar platforms. Its design has made it a favorite among professionals seeking an easy scheduling solution. 

Key features:

  • Easily sync your widgets and add-ons to any landing pages and website.
  • Send a personal calendar link that schedules an event or meeting without time conflicts.
  • Integrate your account with Salesforce, CRM tools, and billing platforms to keep track of your teammates and clients.
  • Create and develop workflows that automatically send emails and texts to your clients/prospects before and after your call.


Basic: Free

  • Connect one calendar
  • Create one event type

Essentials: $8/month

  • Connect six calendars
  • Send invitees email reminders and follow-ups

Profesional: $12/month

  • Create collective event types
  • Build automated workflows and custom notifications

Teams: $16/month

  • Route with Hubspot, Marketo, or Pardot
  • Connect to Salesforce

Going forward

Here’s a recap:

  • Clockwise is best for teams that meet regularly and want to create more time in their day for deep work.
  • Reclaim AI is ideal for individuals who want to time block their tasks automatically.
  • Motion is best for teams looking for an all-in-one calendar app, task and project management tool, and scheduling tool.
  • Calendly is ideal for simple meeting scheduling without the back-and-forth communication.

Read next:

About the author

Judy Tsuei

Judy Tsuei is a Simon & Schuster author, speaker, and podcast host. She’s been featured in MindBodyGreen, BBC Travel, Fast Company, Hello Giggles, and more. As the founder of Wild Hearted Words, a creative marketing agency for global brands, Judy is also a mentor with the Founder Institute, the world's largest pre-seed accelerator. Judy advocates for mental and emotional health on her popular podcast, F*ck Saving Face. Follow along her journey at

Optimize your work day with AI powered calendar automation.

Sign up for free

Make your schedule work for you

More from Clockwise