What Is Sidekick AI ?
Sidekick AI is an intelligent scheduling assistant that automates the meeting booking process through AI-powered features like email parsing, customizable scheduling pages, and team coordination. Designed for individuals and teams, it eliminates the hassle of back-and-forth scheduling by integrating with tools like Google Calendar, Outlook, Zoom, and Microsoft Teams.
Feature Table
| Feature | Details |
|---|---|
| Name | Sidekick AI |
| Founded Year | 2020 |
| Developer | Sidekick AI, Inc. |
| Available Platforms | Web-based, Chrome Extension |
| Primary Use Cases | Meeting scheduling, calendar automation, team coordination |
| AI Capabilities | Natural language processing for email interpretation and smart scheduling |
| Integrations | Google Calendar, Outlook, Microsoft Teams, Zoom |
| User Interface | Dashboard with scheduling links, team calendar views, and analytics |
| Collaboration Tools | Team scheduling pages, group availability sync |
| Customization Options | Personalized scheduling pages, branding (on paid plan) |
| Free Plan Availability | Yes, with generous feature limits |
| Languages Supported | English |
Who Should Use It
Freelancers and Solopreneurs who want automated scheduling without back-and-forth emails.
Remote Teams that need to coordinate across time zones using shared team calendars.
Client-Facing Professionals like consultants, coaches, and sales teams who rely on client bookings.
Small Businesses that want a low-cost AI-powered scheduling tool.
Recruiters and HR Teams handling multiple candidate interviews across different team members.
How to Use (Step-by-Step)
Sign Up: Go to Sidekick AI’s website and create an account.
Connect Calendar: Link your Google or Outlook calendar for real-time availability syncing.
Set Availability: Define your working hours and create personalized scheduling pages.
Try “Forward to Schedule”: Forward any email with scheduling intent to Sidekick, and it will book the meeting for you.
Use Team Scheduling: Enable shared scheduling across your team for coordinated group meetings.
Embed or Share Links: Embed your scheduling pages in emails or websites or send direct links.
Upgrade if Needed: For branding removal, unlimited pages, and deeper analytics, switch to the paid plan.
Pricing Plans
| Plan | Price | Features |
|---|---|---|
| Free | $0/month | 3 personal pages, 1 calendar source, unlimited meetings, auto-scheduling, integrations |
| Paid | $15/month | Everything in Free + AI ‘Forward to Schedule’, unlimited pages/calendars, team features, no branding, stats |
Free vs Paid Comparison
| Feature | Free Plan | Paid Plan ($15/month) |
|---|---|---|
| Scheduling Pages | 3 personal pages | Unlimited personal + team pages |
| Connected Calendars | 1 source | Unlimited |
| Integrations (Google/Outlook) | ✅ | ✅ |
| Auto Scheduling | ✅ | ✅ |
| AI “Forward to Schedule” | ❌ | ✅ |
| Remove Branding | ❌ | ✅ |
| Analytics/Meeting Stats | ❌ | ✅ |
Capabilities
AI-powered email interpretation to schedule meetings automatically.
Custom-branded scheduling pages for personalized client experience (paid).
Syncs real-time availability from multiple calendars.
Group and team meeting scheduling optimization.
Direct integrations with major communication and calendar tools.
Evolution Timeline
| Year | Milestone |
|---|---|
| 2020 | Sidekick AI launches with basic scheduling automation |
| 2021 | Introduced “Forward to Schedule” feature powered by AI |
| 2022 | Added integrations with Outlook, Teams, Zoom |
| 2023 | Launched advanced team scheduling and branding removal in paid plans |
| 2024 | Improved analytics and meeting stats dashboard |
Pros and Cons
| Pros | Cons |
|---|---|
| AI-powered “Forward to Schedule” simplifies email-based scheduling | Branding can only be removed in the paid plan |
| Robust free plan includes unlimited meetings and integrations | Some advanced features may have a learning curve |
| Easy setup and seamless calendar integration | No mobile app as of now |
| Team scheduling feature supports group coordination | Limited customization for scheduling pages on free tier |
Summary for Target Users
Sidekick AI is an ideal solution for individuals, teams, and client-facing professionals who need to simplify and automate the scheduling process. Its standout AI-driven “Forward to Schedule” feature makes it incredibly time-saving, while its strong free plan supports generous functionality. Whether you’re a freelancer, startup, or enterprise team, Sidekick AI helps you schedule smarter, faster, and without friction.
Official Resources
Website: https://www.sidekickai.com
Pricing: https://www.sidekickai.com/pricing
Help Center: https://support.sidekickai.com
Final Verdict
Sidekick AI is a forward-thinking scheduling assistant that delivers exceptional value, especially with its AI-powered email scheduling and team coordination features. With a generous free plan and scalable premium offering, it stands out among other scheduling tools as a smart, efficient, and accessible solution for modern professionals.
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