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Sidekick AI — AI for Personal Productivity & Executive Assistants

Automate meeting scheduling by simply forwarding an email. Reclaim hours spent on calendar coordination.

Sidekick uses AI and language processing to find the best times, send invites, and manage reminders, acting as your virtual scheduling assistant.

What is Sidekick AI?

Sidekick AI: Automate meeting scheduling by simply forwarding an email. Reclaim hours spent on calendar coordination. It has a free plan; paid plans start at $5 month. Zekai's independent review scores it 6.5 out of 10. Best for automating meeting booking via email forwarding.

Facts checked 16 Oct 2026.

Best forAI Productivity Tools
DifferentiatorAI-powered 'Forward to Schedule' feature that understands and acts on email conversations.
ProofClaims to be a leader in AI scheduling, with a unique email forwarding feature.
Try Sidekick AI
Free Plan Pro from$5 month
Free plan verified · free AI tools for Productivity
6.5 Zekai
Your AI Scheduling Assistant
AI for Personal Productivity & Executive Assistants
Ease of Use
7.0
Accuracy
6.6
Value
6.2
Time Saving
6.0
AI SchedulingTeam CalendarsCalendar SyncEmail IntegrationVideo Conferencing
📊 Independently reviewed and scored. How we score →
✍️ Reviewed by Zekai Editorial Team · Updated August 6, 2026
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Zekai Verdict

What is it?
Sidekick AI is a smart scheduling tool for Executive Assistants and busy professionals that automates meeting booking.
Best for
Best for assistants and professionals who want to automate the back-and-forth of email-based scheduling.
Not ideal for
Core 'Forward to Schedule' AI is only available on the paid plan.
Price
Free plan · paid from $5 month
Zekai Score
6.5/10
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Hand-scored by Zekai

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⚡ Quick answer

For Personal Productivity & Executive Assistants, Sidekick AI is a top choice for automating meeting scheduling directly from your inbox. Its unique 'Forward to Schedule' feature allows you to simply forward an email thread, and the AI handles all the back-and-forth coordination, saving significant time compared to traditional booking links.

CategoryAI Scheduling Assistant
Best forAutomating meeting booking via email forwarding.
Price from$5 month
Free planYes
DifferentiatorAI-powered 'Forward to Schedule' feature that understands and acts on email conversations.
ProofClaims to be a leader in AI scheduling, with a unique email forwarding feature.
Rating6.5/10
📖 About Sidekick AI

Sidekick AI is a smart scheduling tool for Executive Assistants and busy professionals that automates meeting booking. It offers multiple scheduling methods, including forwarding an email to the AI, creating shareable scheduling pages, and instant booking between Sidekick users.

How It Works

Your workflow, automated

1
Forward the Email
Forward an email thread about scheduling a meeting to your unique Sidekick AI address.
2
AI Parses & Proposes
Sidekick's AI reads the email, checks your connected calendar for availability, and proposes times to the other participants.
3
Booking Confirmed
Once a time is agreed upon, Sidekick automatically creates the calendar event, sends invites, and sets reminders for all attendees.
Ready to automate your workflow with Sidekick AI?
Try Sidekick AI →
Real Impact

Before & After

❌ Before

Endless back-and-forth emails trying to find a meeting time for multiple people.

10-15 mins per meeting
✅ After

Meetings are booked automatically after forwarding a single email.

<1 min per meeting
Prompt Templates

Try it with these prompts

Copy any prompt and paste it directly into the tool.

Schedule meeting via email forward

Forward this email to Sidekick AI to schedule a meeting. It will analyze the content and suggest optimal times based on my connected calendars. I will then receive a confirmation with the meeting details.

Create a team scheduling page

Generate a Team Page for my team to schedule meetings with external clients or partners. This page will allow multiple people on my team to be available for booking, simplifying coordination for group meetings.

Remove branding from scheduling

Apply the paid feature to remove Sidekick AI branding from my scheduling pages and meeting invitations. This will allow me to present a more professional and white-labeled experience to my contacts.

AI Prompts

Prompts for Productivity

Prompt 01 The 'Find a Time' Multi-Time-Zone Juggler
CONTEXT: I need to schedule a [[DURATION]]-minute virtual meeting for [[EXECUTIVE's NAME]]. The topic is "[[TOPIC]]." This is a [[high/medium/low]] priority meeting.
Prompt 02 The 'Ideal Week' Blueprint Creator
CONTEXT: I am designing the ideal weekly template for my executive, [[EXECUTIVE's NAME]]. Their primary goals are: • Goal 1: [[e.g., More deep work time for strategic planning]] • Goal 2: [[e.g., Shorter, more decisive meetings]] • Goal 3…
Prompt 03 The 'Airtight Meeting Agenda' Generator
CONTEXT: I am preparing for a [[DURATION]]-minute meeting on "[[TOPIC]]." The goal of the meeting is: [[MEETING GOAL]]. Attendees are: [[List of attendees and their roles]].
See all 59 AI prompts for Productivity →
Social Proof

Trusted by professionals

Ease of Use
7.0
Accuracy
6.6
Value
6.2
Time Saving
6.0
Start Free Today →
Connects With

Sidekick AI integrations

Google Calendar Outlook Calendar Microsoft 365 Microsoft Teams Google Meet Zoom Skype Thunderbird
Setup complexity: Easy
Sidekick AI is a smart scheduling tool for Executive Assistants and busy professionals that automates meeting booking. It offers multiple scheduling methods, including forwarding an email to the AI, creating shareable scheduling pages, and instant booking between Sidekick users.
Comparison

Best Sidekick AI alternatives

Sidekick AI vs. Calendly: Choose Calendly for its polished, industry-standard booking pages and robust integrations, ideal for straightforward self-service scheduling. Pick Sidekick AI when your primary pain point is the back-and-forth of email coordination. Its 'Forward to Schedule' feature acts like a true assistant, interpreting requests and managing the booking process for you—a workflow Calendly doesn't offer. While Sidekick has booking pages, its core strength and value proposition lie in its email-based AI automation, making it a better fit for EAs and professionals who live in their inbox.

The decision

Is Sidekick AI worth it?

Return on investment
At just $5/month for the Superhero plan, reclaiming even one hour of scheduling time per month delivers a significant return on investment for any busy professional or assistant.
Built for
Executive Assistants, Personal Assistants, and busy professionals who spend significant time coordinating meetings with internal and external stakeholders.
Effort to adopt
Easy
Compliance
Compliance posture not publicly documented — verify with vendor.
Who It's For

Why Personal Productivity & Executive Assistants choose this tool

🎯
Built for
Best for assistants and professionals who want to automate the back-and-forth of email-based scheduling.
In-Depth Overview
For Executive Assistants and productivity-focused professionals, Sidekick AI's core value is its 'Forward to Schedule' feature. Unlike simply sharing a booking link, this allows you to delegate the entire scheduling task by forwarding an email thread. The AI then uses language processing to understand the context, communicate with participants, and find a mutually agreeable time, effectively acting as a virtual assistant that lives in your inbox. While it also provides standard 'Scheduling Pages' similar to Calendly, Sidekick positions itself as a more comprehensive assistant. The platform supports team scheduling where only the creator needs a paid plan, making it a cost-effective solution for coordinating across departments. It integrates with essential calendars and video conferencing tools (Google, Outlook, Teams, Zoom), ensuring it fits into your existing workflow. By offering multiple ways to schedule—AI forwarding, shareable pages, and instant booking with other Sidekick users—it provides flexibility that reduces the manual, time-consuming effort of calendar management.

Key Use Cases

🗓️
Offload Complex Group Scheduling
Executive Assistant
Forward a chaotic email thread with multiple participants to Sidekick. The AI parses the conversation, identifies availability across calendars, and coordinates to book the meeting without you manually checking schedules.
Reduces scheduling time from 15 minutes to under 1 minute.
📈
Streamline Client Demo Bookings
Sales Professional
Create a dedicated 'Demo' scheduling page with pre-set availability and integrated Zoom links. Share the link in outreach emails to let prospects book a time that works for them instantly.
Eliminates follow-up emails and accelerates sales cycles.
🤝
Coordinate Panel Interviews Efficiently
Hiring Manager
Set up a 'Team Page' for your interview panel. Candidates can select a time that works for everyone on the team, avoiding the headache of cross-referencing multiple calendars.
Improves candidate experience and reduces time-to-hire.
✓ Pros
Unique 'Forward to Schedule' feature automates email-based booking.
Offers multiple scheduling methods (AI forwarding, booking pages, direct sync).
Generous free-forever plan with unlimited scheduled meetings.
Cost-effective team scheduling where only the page creator needs a paid plan.
Integrates with Google, Outlook, Microsoft 365, Teams, Zoom, and Skype.
· Cons
Core 'Forward to Schedule' AI is only available on the paid plan.
Full white-labeling is not yet available, only branding removal.
User interface is functional but less polished than some market leaders.
The 'Sidekick Business' plan is still in a BETA phase.
⚡ Editorial Verdict

Sidekick AI excels with its 'Forward to Schedule' feature, which genuinely feels like delegating to an assistant. While its scheduling pages are competent, the core value lies in its email-based AI. The main trade-off is that its most powerful feature requires the affordable paid plan and a different workflow than standard booking links.

See all 947 AI tools for Productivity → Browse the AI Directory →
Questions & Answers

Frequently asked questions

How is Sidekick AI different from Calendly?

+
Sidekick AI offers similar 'Scheduling Pages' but its main differentiator is the 'Forward to Schedule' feature. This allows you to forward an email to the AI, which then handles the booking process, acting more like a personal assistant than a simple booking link.

Can I use Sidekick AI for team scheduling?

+
Yes. With a paid 'Superhero' plan, you can create 'Team Pages'. You can invite unlimited team members to join a page for free by syncing their calendars; only the page creator needs to have a paid account.

Is there a free version of Sidekick AI?

+
Yes, Sidekick AI offers a 'Hero Plan' which is free forever. It includes one connected calendar source, three scheduling pages, and unlimited scheduled meetings.

Which AI scheduling tool is best for an Executive Assistant?

+
Sidekick AI is an excellent choice for Executive Assistants because its 'Forward to Schedule' feature mimics the act of delegating. You can forward an email thread, and the AI handles the complex coordination, saving significant time compared to manually managing booking links.

What's the best AI to manage my calendar via email?

+
Sidekick AI is designed for this specific task. Its 'Forward to Schedule' feature uses AI and language processing to read your emails and book meetings automatically, making it one of the best tools for managing your calendar directly from your inbox.

How can I automate booking meetings for my team without everyone needing a paid seat?

+
Sidekick AI's team scheduling is very cost-effective. Only one person needs a paid 'Superhero' plan to create a 'Team Page'. Other team members can join and sync their calendars for free, allowing clients or colleagues to book a time that works for the entire group.

Last reviewed:

Plans & Pricing

Sidekick AI pricing and plans

Free
$0
This plan is perfect for heros who need just a little help from a Sidekick with scheduling.
Get Started Free
Pro
$5 month
The Superhero plan includes unlimited calendars, the 'Forward to Schedule' AI feature, team pages, and removal of Sidekick branding.
Start Pro Plan
Enterprise
Pricing on request
Tailored for teams and large organisations.
Contact Sales

Prices and features are updated regularly but can change at any time — always confirm on the official website. Some links on this page are affiliate links.

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Free guide

Take it with you

Getting Started with Sidekick AI
  • Master Email-Based Scheduling: Learn the magic of the 'Forward to Schedule' feature.
  • Set Up Your Public Face: Create polished, effective personal and team scheduling pages.
  • Integrate Your Toolkit: Connect your calendars (Google/Outlook) and video conferencing apps (Zoom/Teams).
  • Understand Your Availability: Configure your working hours and meeting buffers for perfect scheduling.
  • Go Pro with Team Pages: Discover how to manage scheduling for your entire team with a single paid account.
+3 more steps inside the guide
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About Sidekick AI

Full Description

Sidekick AI is a smart scheduling tool for Executive Assistants and busy professionals that automates meeting booking. It offers multiple scheduling methods, including forwarding an email to the AI, creating shareable scheduling pages, and instant booking between Sidekick users.

Editorial Verdict

Sidekick AI excels with its 'Forward to Schedule' feature, which genuinely feels like delegating to an assistant. While its scheduling pages are competent, the core value lies in its email-based AI. The main trade-off is that its most powerful feature requires the affordable paid plan and a different workflow than standard booking links.

Last reviewed:
Disclaimer
Zekai is an independent AI tools directory. We are not affiliated with, endorsed by, or officially connected to Sidekick AI unless clearly stated. All product names, logos, and brands are the property of their respective owners and are used for identification purposes only. The information on this page — including pricing, features, and availability — is general information, may have changed since our last review, and is not professional advice. Zekai Scores and verdicts are our editorial opinion. Some outbound links are affiliate links that may earn us a commission at no extra cost to you. Spotted outdated or incorrect information? Request a correction →
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