Sidekick AI Review: AI-Powered Meeting Scheduling and Calendar Automation
Overview
Sidekick AI is an AI-powered scheduling assistant designed to automate meeting coordination, eliminate scheduling conflicts, and optimize calendar management. Unlike traditional scheduling tools that require users to manually pick times and send booking links, Sidekick AI intelligently schedules meetings based on availability and preferences.
Sidekick AI is particularly useful for professionals, sales teams, and recruiters who want a hands-off scheduling solution that integrates seamlessly with their calendars and email workflows.
Key Features:
AI-powered meeting scheduling: Finds the best time for meetings automatically.
Auto-scheduling via email: Users can forward meeting requests to Sidekick AI, which handles the rest.
Smart availability detection: AI scans users’ calendars to avoid conflicts.
Booking pages & shared scheduling links: Custom meeting links for easy scheduling.
Multi-attendee scheduling: Finds common availability for teams and clients.
Time zone management: Adjusts meeting times automatically for global users.
Calendar integration: Works with Google Calendar, Outlook, and Microsoft 365.
What Is Sidekick AI Best For?
Sidekick AI is best suited for AI-powered scheduling automation, smart meeting coordination, and eliminating back-and-forth emails. It excels in the following areas:
✅ Automatically schedules meetings based on availability.
✅ Eliminates scheduling back-and-forth by handling email requests.
✅ Syncs with Google Calendar, Outlook, and Microsoft 365.
✅ Provides scheduling links for self-booking.
✅ Time zone adjustments ensure smooth coordination for global teams.
However, Sidekick AI does not offer deep workflow automation or task management, making it less ideal for users who need a broader productivity suite.
Who Would Benefit Most from Sidekick AI?
Sidekick AI is particularly useful for:
🔹 Sales & customer success teams: Automates client meeting bookings.
🔹 Executives & entrepreneurs: Manages schedules without manual effort.
🔹 Recruiters & HR professionals: Schedules interviews effortlessly.
🔹 Freelancers & consultants: Streamlines client bookings.
🔹 Remote & hybrid teams: Schedules meetings across different time zones.
While great for meeting automation, users needing task prioritization, deep CRM integrations, or project management tools may prefer alternatives like Motion AI or Reclaim AI.
Reviews Across the Internet
Sidekick AI has received positive feedback on Reddit, particularly from users who appreciate its auto-scheduling via email and booking link flexibility. However, some users mention limited customization and occasional AI scheduling conflicts.
Pros (per Reddit users):
✔️ Automated email scheduling is a time-saver.
✔️ Booking links make self-scheduling easy.
✔️ Good for handling multi-attendee meetings.
Cons (per Reddit users):
❌ Limited customization options for scheduling preferences.
❌ Occasional scheduling conflicts require manual adjustments.
❌ No task management or deep workflow automation.
Trustpilot
Sidekick AI holds an average rating of 4.2–4.5 stars, with users praising its automation, ease of use, and email-based scheduling capabilities. Some mention pricing concerns and occasional AI scheduling errors.
Common Praise:
✔️ Eliminates manual scheduling effort.
✔️ AI handles email-based meeting coordination smoothly.
✔️ Syncs well with calendars and time zones.
Common Criticism:
❌ AI may not always schedule meetings at the ideal time.
❌ Lacks broader workflow automation or integrations.
❌ Premium pricing may not be ideal for casual users.
G2 & Capterra Reviews
G2 rating: ~4.3/5.
Capterra rating: ~4.2/5.
General sentiment: Highly rated for AI-powered scheduling, but some users desire more customization.
Pricing Structure
Sidekick AI follows a subscription-based pricing model with different tiers.
1. Free Plan (Limited Features)
✅ Basic meeting scheduling
✅ Google & Outlook calendar integration
✅ Limited AI automation
2. Pro Plan ($8/month per user)
✅ Unlimited AI-powered scheduling
✅ Auto-scheduling via email forwarding
✅ Custom booking links & meeting preferences
✅ Time zone detection & multi-attendee scheduling
3. Business Plan ($15/month per user)
✅ Advanced team scheduling coordination
✅ Recurring meeting automation
✅ Priority customer support
4. Enterprise Plan (Custom Pricing)
✅ API access & workflow automation
✅ Dedicated customer support & security compliance
✅ Custom integration with business tools
💡 Note: The free plan offers basic scheduling, while paid plans unlock full AI-powered meeting automation and customization.
Best Use Cases to Demonstrate Sidekick AI’s Power
1. AI-Powered Sales Call Scheduling
Sales teams can use Sidekick AI to automate prospect call scheduling, ensuring high-priority leads get booked first.
2. Automated Interview Scheduling for Recruiters
HR professionals can allow Sidekick AI to coordinate interviews and manage rescheduling requests automatically.
3. Hands-Free Meeting Coordination for Executives
Executives can delegate scheduling to Sidekick AI, reducing administrative workload.
4. Client & Consultant Appointment Management
Freelancers and consultants can send booking links to clients or let Sidekick AI handle scheduling via email.
FAQs
1. How does Sidekick AI work?
Sidekick AI analyzes users’ calendars, meeting requests, and availability, then automatically schedules meetings via email interactions or booking links.
2. Can I manually override Sidekick AI’s scheduling?
Yes, users can adjust meeting preferences and availability settings, but AI will still optimize scheduling based on available slots.
3. Does Sidekick AI integrate with CRM or task management tools?
No, Sidekick AI primarily focuses on scheduling and does not integrate deeply with task management tools like Asana or Trello.
4. Is Sidekick AI secure?
Yes, Sidekick AI follows standard encryption and compliance measures to protect user data.
5. Can I use Sidekick AI for free?
Yes, but the free plan has limited scheduling capabilities and lacks advanced automation features.
6. How does Sidekick AI compare to Calendly?
Sidekick AI automates scheduling via email, while Calendly requires users to book through links.
Calendly is better for manual scheduling control, while Sidekick AI offers a more hands-off experience.
Sidekick AI is better for email-based scheduling automation, whereas Calendly is better for direct user control.
7. Does Sidekick AI support team collaboration?
Yes, the Business and Enterprise plans include advanced team scheduling and workflow automation features.
8. Does Sidekick AI support API access?
Yes, Enterprise users can integrate Sidekick AI into their workflows using API access.
Final Thoughts
Sidekick AI is a powerful AI-driven scheduling assistant that automates meeting coordination, optimizes availability, and eliminates back-and-forth emails. It is especially useful for sales teams, recruiters, executives, and remote teams who need seamless AI-powered scheduling.
However, users who prefer full manual control over their schedules may find Sidekick AI’s automation too rigid, and its pricing is higher than basic scheduling tools like Calendly. While Sidekick AI excels at AI-powered meeting automation, users who need task management, CRM integrations, or workflow automation may prefer alternatives like Motion AI or Reclaim AI.
For users who want an AI-powered scheduling assistant that automates email-based meeting coordination, Sidekick AI is a strong contender—but those looking for more flexibility or a free scheduling tool may prefer Calendly or Clockwise AI.
