Top 12 Calendar Scheduling Apps of 2024 | Cirrus Insight

As a busy Sales Leader, you are likely continuously looking for opportunities to optimize your team's efficiency. This can be accomplished through several different areas and touchpoints in the sales funnel. However, we have found that optimizing and automating that first touch point, scheduling the first sales call, can be the most impactful and influence the remainder of a prospect's journey. 

There are many calendar scheduling apps available these days and it can be hard to discern what will truly work best for your team. You must consider the limitations of the platform such as booking limits, as well as, what features your team needs. Features such as shareable links and custom lead assignment logic can make a real difference in the effectiveness of your sales team. 

The right calendar scheduling tool is invaluable to growing your team’s efficiency and speed at which a prospect is qualified and enters your pipeline. Benefits of the right tool include increased conversion rates and a streamlined buyer’s journey for your prospect. 

Being the fastest sales team to respond to a prospect is your competitive advantage and streamlining your user experience helps to achieve that. Below, we review the best calendar scheduling apps for sales in 2024 to start accelerating your pipeline today. 

Best Calendar Scheduling Apps of 2024

Cirrus Insight

Free Trial: Yes

Base Paid Plan Price: Starting at $14 per month.

Cirrus Insight Integrations: Salesforce, Google Calendar, Microsoft 365, Microsoft Outlook.

Reviews and Ratings: 1400+ Reviews on G2, and 4.8 Stars on Salesforce AppExchange

Cirrus Insight Smart Scheduler is popular with Sales Operations, Revenue Operations, Marketers and Sales Leaders because it connects qualified prospects on your website directly to the appropriate salesperson’s calendar. Thus avoiding wasted opportunities.  

Highly customizable, Smart Scheduler allows you to intelligently match customers with staff based on personalization criteria, availability and utility. 

Most often used by competitive sales and marketing teams serving high revenue prospects.Some additional features of Smart Scheduler:

• Workflow Groups: Organize people and teams based on your customer acquisition, onboarding or retention journey.

• Availability Matching: Never have to reschedule by ensuring your customer’s and your people’s availability overlap.

• Utilization Logic: Ensure you always have an even distribution of bookings across the entire pool of people.

• Automatic Invites: When customers book, they automatically receive an invite as if a human has scheduled the meeting.

• Web Enabled Smart Forms: Present customers or schedulers with form data required to match them to resources based on any criteria.
• Meeting Form Data: Collect information from your customers dynamically so that you can be better prepared for every meeting.
• See the Cirrus Insight Smart Scheduler in action

Cal.com (formerly Calendso)

Free Team Plan: No

Base Paid Plan Price: $15/seat per month.

Cal.com Integrations: Salesforce, Google Calendar, Apple Calendar, Microsoft Outlook.

Best features: Private single-use scheduling links and Webhooks.

Ratings: 4.8 Stars on Product Hunt

Cal.com is an open-source calendar scheduling app with customization features. Cal.com simplifies scheduling meetings for teams and businesses alike.

Additional features:

• Booking Limits: Decide how many times someone can schedule a meeting with you in a day, week, or month.
• Multi-Calendar Sync: Connect multiple personal and work calendars to prevent scheduling conflicts.
• Workflow Automation: Build processes around your events with custom triggers that automate booking, notification, and cancellation actions.
• Payments: Get paid for your meetings via Stripe.
• Opt-In Bookings: Reject unsolicited booking requests to keep your calendar clutter-free.

Calendly

Free Team Plan: No

Base Paid Plan Price: $20/seat per month.

Calendly Integrations: Salesforce, Google Workspace, Slack, LinkedIn, Microsoft Teams, Microsoft Outlook, Intercom, HubSpot.

Best features: Pre-defined availability schedules and follow-up automation.

Ratings: 4.7 Stars on GetApp

Suited for small business, Calendly ensures efficient time management in customer scheduling.

Some additional features:

• Multi-Calendar Sync: Connect up to six calendars per team member to reduce scheduling conflicts or missed meetings.
• Third-party Form Integrations: Import form fields from existing HubSpot, Pardot, and Marketo workflows.

Zoho Bookings

Free Trial: Yes, with limitations

Base Paid Plan Price: $12/seat per month.

Zoho Bookings Integrations: Google Workspace, Microsoft 365, Microsoft Outlook, Salesforce Sales Cloud.

Key features: On-the-go calendar management with multi-lingual support.

Ratings: 4.5 Stars on GetApp

The Zoho Bookings calendar scheduling app features customizable booking pages

Some additional features:

• Personal Pages: Give your team members their own booking page to share with customers.
• Multi-lingual Support: Zoho Bookings supports Mandarin, German, Japanese and over six other languages.
• Payment Deposits: Choose to get paid in full or collect deposits when your customers book meetings.

ZenCal

Free Team Plan: No

Base Paid Plan Price: $10/seat per month.

ZenCal Integrations: iCloud Calendar, Stripe, HubSpot, Zoom, Zapier.

Key features: Paid meeting subscriptions and customized booking pages for small businesses.

Ratings: 4.9 Stars on Product Hunt

Zencal offers calendar scheduling to businesses offering unpaid meetings. The calendar app also offers pop-up calendar windows.

Some additional features:

• Calendar Overlay: Have your guests safely connect their Google and Outlook calendars on the booking page to see conflicting event slots.
• Custom Cancellation Policy: Create custom rules for consultation scheduling, rescheduling and cancellation to manage last-minute meetings.
• Meeting Subscription and Packages: Sell your meetings in bundles with automatic scheduling and payment reminders.
• Invoicing: Invoice your clients automatically with multiple payment methods and sync all financial details with your accounting software of choice.

Doodle

Free Team Plan: No

Base Paid Plan Price: $19.95/seat per month.

Doodle Integrations: Microsoft Teams, Outlook, Google Meet, Zoom, Zapier, iCloud, Webex.

Best feature: Group polls with deadlines and reminders to pick the best time to meet.

Doodle facilitates easy meeting scheduling for teams, businesses, and everyone in between. 

Ratings: 4.6 Stars on GetApp

Some additional features:

• Privacy: Doodle lets you hide your meeting participants' information.
• Sign-up Sheets: Create a custom registration page for online and in-person events. 
• Export Event Data: Export your event details and user responses to an Excel sheet or PDF document.
• Custom Forms: Collect necessary participant information through custom forms.
• Group Polls: Invite multiple people to vote on what time works best for a meeting or an event without waiting for decisions over email.

Setmore

Free Plan: Yes, with limitations

Base Paid Plan Price: $9/seat per month.

Setmore Integrations: HubSpot, Zoho CRM, Square, Stripe, PayPal, LawPay, WordPress, Wix, Weebly, Squarespace, Zoom.

Best feature: Easy-to-use calendar scheduling interface.

Setmore is a calendar scheduling app for processing payments, collecting reviews and managing client information.

Ratings: 4.7 Stars on GetApp

Some additional features:

• Buffer Times: Setmore allows you to account for travel time and equipment set up in your schedule for out-of-station client appointments.
• Class Booking: Reserve seats for group training events and webinars.
• Recurring Appointments: Give VIPs priority access to your calendar with multiple repeat appointments in one booking.
• Payments: Require full or partial payment via Square or Stripe integrations before confirming appointments to reduce no-shows.

Appointy

Free Trial: Yes, with limitations

Base Paid Plan Price: $59.99 per month for up to five seats.

Appointy Integrations: Facebook, Twitter, iCal, Zapier, Google Analytics.

Best feature: Multiple slot reservations for meetings and events.

Appointy is an event management tool for service-based businesses and professionals.

Ratings: 4.6 Stars on GetApp

Some additional features:

• Booking Promotions: Offer exclusive last-minute deals to all your customers through Facebook or Twitter promotions in slow periods or when someone cancels last minute.
• Business Analytics: Track staff performance and compare it with overall organization performance. Monitor appointments, sales, and client growth with graphical comparisons for week-on-week, month-on-month, or year-on-year trends.
• Mobile Admin Console: Instantly access customer performance data, including buying preferences and purchase history to personalize their experience. Automatically group customers based on activity, feedback, and history to optimize service and special offers.
• Multi-lingual Support: Appointy’s booking pages support 20+ languages so you can reach out to your customers in their language.
• Inbuilt Tools: Customize and send invoices with your business details, logos, and preferred layout. Gather reviews, send and track both email open rates and booking conversions with the inbuilt email, accounting and marketing tools.

Chili Piper

Free Plan: No

Base Paid Plan Price: $22.50/seat per month.

Chili Piper Integrations: Salesloft, HubSpot, Outreach, Marketo.

Best feature: Booking meetings on behalf of other people in your team or organization.

Chili Piper is one of the most expensive scheduling apps available.

Ratings: 4.4 Stars on GetApp

Some additional features:

• Hot Handoffs: Chili Piper Handoff automates routing meetings and leads from SDRs to AEs.
• Automated Admin Tasks: Automate routine tasks like sending reminders, scheduling, routing calls and follow-ups.
• Lead Routing and Distribution: Match inbound leads to the right account and remove offline sales reps from your lead router when they’re OOO.
• Form Integrations: integrates with popular forms like Clearbit, ClickFunnels, Formstack, Unbounce and more.

Sign In Scheduling (formerly 10to8)

Free Trial: Yes

Base Paid Plan Price: $460 per year per site.

Sign In Scheduling Integrations: PayPal, Stripe, Zoom, iCal, Microsoft Teams, Zapier.

Key feature: AI-powered calendar scheduling and appointment management.

Ratings: 4.7 Stars on GetApp

Sign-In Scheduling offers self-service options for customers to book, reschedule and cancel physical and virtual appointments without your help. 

Some additional features:

• Bulk Edits: Easily update and manage your services, staff and integrations across all business locations from one centralized panel.
• Unlimited Services: Offer as many services as you have on your online booking page.
• Group Bookings: Schedule individual or group bookings to suit your business needs.
• Analytics: Gain actionable insights on bookings, peak periods, popular services, staff performance and even reports on no-shows for informed decision-making that drive ROI and revenue.

SimplyBook.me

Free Team Plan: No

Base Paid Plan Price: $8.25 per month for up to five seats.

SimplyBook.me Integrations: Google Workspace, Microsoft 365, 

Key feature: Facebook, Instagram and Google My Business booking buttons.

Ratings: 4.6 Stars on GetApp

SimplyBook.me is perfect for small businesses and client-facing service industries that require appointment scheduling and payment collection systems in one tool.

Some additional features:

• Custom Booking Pages: Customize your booking calendar with drag-and-drop functionality for static pages.
• Automated Reviews: Request feedback after appointments to share on your booking page.
• Loyalty Program: Reward loyal clients with coupons, gift cards and loyalty points that stack up as they book appointments with you.
• Admin and Employee Management: Under one dashboard, view and edit your schedule, upcoming meetings, client profiles, and tickets as well as employee schedules, breaks, vacations, and responsibilities.
• Installment Payments: Collect payments in installments or in full via Apple Pay, Google Pay, or your preferred payment provider.

SavvyCal

Free Team Plan: Yes

Base Paid Plan Price: $12/seat per month.

SavvyCal Integrations: iCloud Calendar, Fastmail, Zoom, Google Meet, Microsoft Teams, Slack, HubSpot, Podia, Whereby.

Key feature: One-click access to scheduling links from Google Chrome, Edge or Brave browser extensions.

SavvyCal is a simple scheduling app that prioritizes your productivity while keeping your calendar clean and tidy.

Ratings: 4.4 Stars on GetApp

Some additional features:

• Factor in External Participants: People outside your organization can add their available or busy times to your SavvyCal bookings.
• Stripe Integration: Link your bookings to a corresponding Stripe product and collect for payment before making reservations while also automatically handling taxes through Stripe Tax (for EU customers).
• Availability and Frequency Limits: Rank your preferred availability and cap the number of meetings allowed per day, week, and month — so you can focus.
• Clustered Meetings: Encourage scheduling meetings close to existing ones to avoid calendar gaps.
• No-code Workflow Automation Templates: Create reusable automation for CRM syncing, to-do lists, and other project management tasks.

Features of Calendar Scheduling Apps Beneficial for Sales

Syncing with Multiple Calendars

What happens when you set an important meeting for the same time your child’s having their first soccer game because the slot was open on your work calendar? Or scheduling two high-priority appointments in the same hour?

A must-have feature for calendar scheduling apps is the ability to sync with multiple calendars to get you out of any scheduling conflict.

Time Zones Support

Having out-of-state attendees do quick time conversion math before booking appointments with you can get tricky.

Calendar apps with time zone support ensure accurate and hassle-free scheduling by displaying available times in the user’s local time zone.

User-Friendly Interface

With user-friendly interfaces that simplify scheduling, you, your team members and your clients can easily book appointments without needing advanced technical skills.

Some user-friendly features of calendar scheduling apps include intuitive booking pages, clear organization, and straightforward controls for seamless meeting scheduling.

Implementing a Calendar Scheduling App into Your Sales Strategy

Use Buffer Times

Meetings rarely finish at the allocated hour. And when you have little to no time to catch your breath between calls, overwhelm sets in.

Create buffer times in your calendar scheduling app to avoid overbooking and to absorb the overruns between the end of one meeting and the start of another. This could range from a couple of minutes to some hours.

Buffer times also provide a space to mentally prepare for your next meeting without derailing your entire schedule.

Set Custom Availability Slots

Many free calendar scheduling apps define specific times when you're available for meetings but not a lot of apps allow you to categorize your availability slots.

Instead of manually blocking off time every time you have to share your booking page, use a calendar scheduling app that can create custom availability slots for different purposes and clients — like lead qualification or deal closure. This way, you can display certain times to certain people to either maintain privacy or look busy when you need to, while still being honest about your availability.

Integrate with your CRM or Project Management Software

Calendar scheduling apps sync relevant customer data between third-party tools like your CRM, project management software, and even emails for a clear overview of your sales workflow and commitments.

Tools like Cirrus Insight Salesforce Sync match your appointments to the right lead, contact and account records in Salesforce, eliminating the need for manual data entry and duplicate information management across your sales tech stack.

Set Meeting Agendas

By knowing the agenda in advance, attendees can manage expectations and prepare to make the best of the allotted time. Agendas also reduce meeting fatigue and set the stage for clear next steps at the end of every meeting.

Choosing The Best Calendar Scheduling App for Your Sales Strategy

Having a reliable calendar scheduling app is like having a virtual assistant behind-the-scenes, keeping your meetings orderly and chaos-free.

Tools like Cirrus Insight take it a notch higher by helping you maintain peak productivity while simplifying the process of booking meetings that drive revenue for your organization.