AI Calendar Tools for Executive Assistants: Your New Secret Weapon
Scheduling is an art form. And Executive Assistants? We’re Picasso with a planner.
But even the greats need better brushes and in today’s world, the best tools are AI-powered.
Whether you’re battling back-to-back Outlook invites or living your best Google Calendar life, the right tech can turn calendar chaos into calendar clarity.
I’ve rounded up some of the best AI-driven calendar tools on the market today. Every tool on this list brings something powerful to the table and depending on your setup and style, each one could be a total game-changer.
Here’s your guide to modern scheduling magic, featuring tools trusted by EAs and executive teams at some of the world’s top companies.
Contents:
ShareCal
The Microsoft Must Have
ShareCal is an AI calendaring platform created exclusively for EAs on Outlook. It’s been getting rave reviews from EAs at top companies for its time-saving scheduling features, email drafting + time zone conversions, and AI calendar assistant.
Built for Microsoft users, this tool allows seamless calendar sharing without IT tantrums. Think visibility, efficiency, and fewer “What time works for you?” emails.
Here’s a quick demo to learn more! You can also get in touch with them if you need help with building a business case or getting IT approval.
đź’› Why You’ll Love It: It plays beautifully with your Microsoft environment and turns Microsoft calendars into something that actually feels intelligent, adaptable, and shockingly EA-friendly.
Vimcal
Where Beauty Meets Speed
Vimcal EA is tailor-made for Executive Assistants. It comes with instant cross-timezone scheduling, polling, executive calendar audits, and a mobile app that was featured by Apple.
Think smart shortcuts, instant timezone conversions, and a UI that doesn’t feel like 2011.
Their new Calendar Audit feature gives you a high-level view of how your (or your exec’s) time is actually being spent. Think colour-coded clarity and data-driven decisions instead of gut instinct and crossed fingers.
Vimcal's founders were formerly engineers and PMs at Microsoft (Outlook), Apple, and Twitter, bringing their product expertise to empower C-Suite EAs at enterprises like Nvidia and Zapier.
Plus, you’ll love:
- Slots & Holds for flexible but protected time management (hello, pre-meeting prep).
- Time Travel, which lets you view and book across time zones like a wizard.
- Group Polls, making it easy to find a time that works without the dreaded 47-email chain.
đź’› Why You’ll Love It: The “book me” link alone is enough to change your scheduling life. Add the aesthetic and it’s basically the calendar version of a dopamine hit.
Cabinet
EA Meets Engineer
Cabinet is a scheduling and executive management platform built for executive assistants. Founded in 2018 by an EA and a software engineer, Cabinet saves time, reduces scheduling errors, and frees up capacity for more strategic work.
It integrates seamlessly with Google and Outlook, and includes features like 1:1 and group scheduling links, shadow holds, meeting logs, executive profiles, and instant calendar audits. They even offer a Certification Program to help EAs quickly master the platform.
Not just a calendar—more like a superpowered sidekick for assistants who run the show.
đź’› Why You’ll Love It: Because it was literally made with you in mind.
Sundial
Google Chrome Extension
Sundial is a rising star built for the EA who’s juggling five calendars, three time zones, and a CEO who thinks “flexible” means “free.”
It adds AI tools for high-performing EAs directly inside Google Calendar. It helps EAs save time scheduling with the speed, control and personability they need, without leaving Google Calendar's powerful features.
No more bouncing between inboxes and calendars trying to find overlap—it does the heavy lifting for you with beautiful precision.
With powerful scheduling workflows and clean design, Sundial is a strong contender for assistants who want control, clarity, and calm.
Key features:
- Unlimited timezones in Google Calendar.
- Writes time slots. No timezone errors. Personalize text format.
- Create & bulk delete calendar holds.
- Detects times from emails and overlays them on Gcal.
đź’› Why You'll Love It: It’s like having a second brain dedicated solely to scheduling—intuitive, collaborative, and blissfully efficient. Gmail users will rejoice.
Execify
Revolutionizing The Executive Office
Execify is an AI-powered platform built for the next evolution of executive support. It was a hard one to place on this list because it's so much more than a calendar.
Designed for EAs and Chiefs of Staff, it combines smart scheduling, meeting optimization, and AI-driven task management to elevate operational efficiency across the executive office.
Execify isn’t just about finding gaps in the calendar—it’s about spotting opportunities, eliminating inefficiencies, and helping leaders stay focused on what matters most.
đź’› Why You'll Love It: Execify doesn’t just help you book time—it helps you win time back. Designed for assistants and exec teams who think two (or ten) steps ahead.
Calendly
The Scheduling OG
We couldn’t do this list without including Calendly. It's not your classic EA tool, but for solopreneurs and small teams, it's still a reliable, low-fuss way to handle meeting bookings.
đź’› Why You’ll Love It: Because “Let me know what time works for you” is a sentence we never want to type again.
There you have it. Your curated guide to some of the smartest, most useful calendar tools available right now. Whether you're using Microsoft, navigating Google Workspace, or juggling ten execs and three time zones before your second coffee, there’s something here to make your life easier.
Save this list. Share it with your fellow assistants. Refer back when you’re reviewing tools with your team or trying to streamline your tech stack. Because staying ahead of the curve is part of what makes EAs indispensable.
You’re already brilliant. These tools just help make that brilliance even more efficient ✨
