The Best Calendaring Software for Small Businesses (Free and Paid)

Samir Sampat

Using calendaring software or apps offer a number of advantages over traditional calendars and make it much easier to find a time you are free to collaborate with others. These apps usually allow you to use them through a browser and software on your computer as well as a mobile app.  

The best options on the market today integrate well with the apps you already use, send reminders through email and SMS messages, allow you to share your calendar with other users, and more.  

For even better calendar management, you may want to consider delegating some of your appointment-setting tasks. Smith.ai provides several services and solutions for small business owners who juggle a busy calendar.

Calendaring Programs: The Calendar Hosts

When it comes to calendaring software, there are two types to consider. One type of calendaring program hosts your calendar and serves as a foundation that the other scheduling and calendaring programs work on top of. Millions of businesses, large and small, rely on all three of these options for hosting their calendars.  

  • Microsoft Outlook has been around since 1990. It works efficiently with many of the programs likely already on your computer, including Office Suite, email, calendar, contacts, and more. It is sometimes known as Office 365.  
  • Google Calendar was designed for teams to use together, making it easier to collaborate. It works in any browser, in addition to an app on a computer, tablet, and smartphone. There is integration with all other G-Suite apps, including Drive, Hangouts, Gmail, and more.  
  • iCalendar has an intuitive and easy-to-use interface that allows you to identify booked times and free times quickly and also to add events and meetings with little effort. It integrates with the most popular services, including Google, Exchange, and Outlook. It is a universal app. You will only need to download it once to use on all your devices and laptop.

Calendaring Software for Your Small Business

Many of the most popular calendaring software and apps provide a free trial or a limited free version. For some small businesses, this free version may offer all the features necessary. This is especially true if you are a sole proprietor or the only staff member who meets with clients.  

In some cases, paying the relatively nominal fee for access to a full-powered calendaring app may be a good option. These programs generally cost under $20 a month, and some provide unique features that could make your life easier.

  • Calendly is an intuitive, easy-to-use scheduling tool. They offer Basic, Premium, and Pro levels, depending on how many users you will have and the features you need to access. This is one of the best options for a busy office when several people need to share spaces, collaborate, or manage dozens of appointments each week.  
  • Appointy has a free version that is likely best for solo-entrepreneurs or small businesses with only one administrative officer since the free version only allows for one calendar. You can book up to 100 appointments per month. It integrates with third-party software, including Google Calendar, and offers both email and SMS reminders. Zoom integration requires an upgrade to the paid version, which is also a good option for larger teams.
  • ScheduleOnce can be used to let customers schedule appointments with a business. You can set availability times and include secure video links, such as to Zoom or Google Meet. Users can choose to have a free basic plan or a monthly Teams plan if they have a small business. Larger companies can contact ScheduleOnce for a direct quote based on their needs.
  • Woven gives users smart templates to use when scheduling events and allows access to multiple calendars. Woven’s Calendar Graph also allows individual users to show their availability, which can make scheduling events much easier. Woven offers a free 21-day trial to their premium plan, which is $15 a month.
  • Calendar integrates analytics and productivity tools to allow you to schedule meetings, events, and other time blocks without risking double-booking or becoming overburdened with tasks. The analytics tools use artificial intelligence to study your work patterns and can alert you of ways to improve your schedule. There are basic, standard, and pro plans, with prices ranging from free to $8 a month.
  • 10to8 offers a free version that integrates well with many third-party applications and software programs, including the most commonly used business apps. The free version offers two calendars, up to 100 appointments per month, and sends out email and SMS reminders about appointments. The paid version provides additional calendars. The 10to8 app is available on Windows, macOS, iOS, and Android.
  • Acuity Scheduling allows not only scheduling appointments but also accepting payments and completing intake forms, all online and around-the-clock. This program has a seven-day free trial and a free version with limited features.
  • Appointlet has a free version, but the full features offered with the paid version are much better. This includes team scheduling features and video meeting integration. You can put your logo or other branding on your own customized booking page for your website or in emails. The software also allows you to accept payments.
  • Lightning Calendar from Thunderbird, a free email application subsidiary of Mozilla, allows you to organize multiple calendars, plan events that you can invite friends to, and make to-do lists. You can also subscribe to public calendars.
  • Fantastical by Flexibits can be a great calendaring app if your business runs on MacOS. Its user interface works on multiple Apple products and allows you to view multiple schedules, including other widgets you’d like to see on your device. Fantastical also detects various types of conference calls, making it easier to send links and directly start your calls. Also personal touches include time zone compatibility, family planning, and weather updates.  

Smith.ai integrates with many other calendaring programs, as well. There are many great options for scheduling and taking care of other calendar-related tasks available today. They all have pros and cons, but there is sure to be one that fits your business’s needs.  

Smith.ai Offers Services and Solutions to Support Small Businesses  

As a small business owner, your calendar is likely always full. You have a hand in every aspect of managing your company, and there is rarely any downtime to figure out how to make things easier on yourself. This is where Smith.ai comes in. With the services and solutions we offer in plans, we can help you run your business more efficiently and give you time to focus on the really important tasks. Our plans are easy to understand and we offer month-to-month contracts for your convenience.

When it comes to managing your calendar and growing your small business, our team offers services that include:  

  • Appointment Scheduling: We will manage incoming or outgoing calls, book appointments for you, and can put them on the calendar you already use, in most cases.
  • Lead Screening/Intake: We manage incoming messages, chats, texts, emails, and other contacts, pre-qualify them based on the criteria you set, and call for a consultation with you or one of your team members only if they meet the criteria.
  • CRM Integration: Our contacts with your clients, customers, or potential customers are all automatically logged into your own system. Our services integrate seamlessly with most of the popular CRM technology.
  • Temporary Receptionist: We ensure your incoming calls are answered by a real person 24/7, including when your team is on lunch, on vacation, in a meeting, or otherwise unavailable.

Let Our Team Discuss How We Can Help Your Business Grow

At Smith.ai, our team advocates for business owners and administrators not having to handle every task on their own. We believe you can better focus on growing your business when you delegate, automate, and have the right smart systems in place to support you. We manage many aspects of calendaring to the companies we serve, from conference calls with a Smith.ai operator to adding video meetings to your calendar.

We provide 15-minute consultations for small businesses and large corporations alike, helping you understand our services and solutions. With our upfront plans and pricing, you may opt for a suite of services, a single service, or a custom plan and get started right away. You can reach a representative from the Smith.ai team now. You can call or text (650) 727-6484, email hello@smith.ai, or use the website chat to schedule a time to get started.  

Samir Sampat

Samir Sampat is a Marketing and Events Associate with Smith.ai. He has experience working with businesses of all sizes focusing on marketing, communications, and business development.

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