The past decade has seen the widespread adoption of cloud-based productivity tools, enabling workers to streamline manual tasks and become more efficient. This shift towards automation is key in allowing workers to redirect their attention towards higher-value tasks and meet the demands of a fast-paced work environment, where 46% of individuals feel they lack sufficient time in a 40-hour workweek. Workers feel the pressure to be productive, so 76% of employees are willing to invest their resources in productivity tools that save time.

Excessive emails, scheduling challenges, and suboptimal meeting timing decrease productivity in the workplace. The back-and-forth emails it takes to schedule a meeting are typically a source of frustration. This universal pain point leads to a global market opportunity because meeting scheduling touches many industries, use cases, and business processes. The appointment scheduling software market size is expected to increase by $633 million from 2020 to 2025, and 39% of the market's growth will come from North America during the forecast period.

Calendly is an automation platform that allows users to schedule meetings easily. It has over 10 million users worldwide, and 200 million meetings have been scheduled using Calendly as of 2022.

Calendly, a company based in the Atlanta area, was founded in 2013 by Tope Awotona. Awotona grew up in Nigeria and moved to the US as a teenager. After graduating from the University of Georgia, he landed a job at IBM as a sales rep. He spent the next seven years in sales across several companies, but had always wanted to become an entrepreneur. He spent his evenings and weekends trying to build a business.

Before landing on the idea for Calendly, he tried his hand at building three other businesses. First he tried to build a dating site, but quickly realized he didn't have the resources or skills and so he never launched the business. His second startup was a website selling projectors. However, not many sold, and the margins weren’t good. His third startup was an ecommerce website selling grills. Awotona realized he kept doing things he wasn’t passionate about and that his previous efforts had been only about starting a business to make money, but he knew that wasn’t working. He decided his new focus would have to be something he knew about that could solve a significant problem.

The idea for Calendly came from Awotona's frustration with scheduling meetings as a salesman. He found that coordinating times and finding availability between multiple people was time-consuming and often resulted in back-and-forth emails and phone calls. He found the existing tools clunky. Realizing there was a need for a simpler and more efficient solution, Awotona decided to start Calendly in 2013, investing $200K of his savings to develop the product.

Calendly’s product is intended to help people book meetings faster and easier.

Users can sync their Google, iCloud, or any other calendar and Calendly will give them a link or embed that they can send to people they want to meet. The senders can customize their availability through scheduling rules and buffers. The recipient can then use that page to choose a time to meet. It then auto-generates a calendar invite for that event and sends it to both parties.

Calendly also offers the option to add one-click scheduling to a user's website, with the goal of improving lead times and increasing conversion rates.

Source: Calendly

Both individuals and teams can use Calendly. For teams, Calendly aims to enhance the efficiency with which teams can spend time with each other and external parties. Large teams have unique scheduling requirements. Calendly equips these teams to create stronger connections with customers and prospects, increase engagement, and close more deals.

Source: Calendly

Calendly for Teams offers the following:

• Personalized scheduling page - Invitees can access and choose from meeting types based on their needs. Team pages can display a variety of meeting choices, letting invitees schedule based on the nature of the meeting. Users can mix and match meeting types to offer a variety of hosts and availability.

• Multi-person Scheduling - Pools the scheduling availability of a team together to offer more options to connect.

• Workflows - Notifications, reminders, and follow-ups for various event types via SMS or emails. Users can automate routine communications before and after every meeting – leaving the team with more time and energy for work.

• Analytics & Reporting - A customizable dashboard to track activity and patterns across event types, filtered by individuals, teams, or groups. This also helps with capacity planning and figuring out day-to-day team availability based on meeting trends.

• Integrations - Connections to tools the team uses for work across categories like communications, calendars, CRM, analytics, ATS, and more to streamline work.

Source: Calendly

Calendly is designed for teams to conduct meetings at scale. It is used across sales, marketing, customer support, and recruiting functions.

Source: Calendly

Calendly for Enterprise has all the teams-based scheduling features, emphasizing efficiency, scalability, and security. With Enterprise, customers get a dedicated account partner to review customers’ goals and help optimize Calendly to meet them. The admins can automatically onboard and offboard users from the organization’s account to better safeguard company data. The single sign-on ensures members of the organization access Calendly using credentials consistent with their identity provider. Calendly’s data deletion feature enables admins to remove user data from one centralized place to meet compliance requirements.

Customer

Calendly caters to anyone in an organization for internal meetings and to people in externally facing roles with frequent meetings for work.

• Sales teams use Calendly because speed is key to landing deals. It enables salespeople to respond quickly to customer requests. The tool syncs with CRM systems, ensuring that meetings are accurately recorded.

• Marketing teams mainly use the tool to schedule meetings with agencies, partners, and vendors.

• Customer Success teams are responsible for improving customer experience and are expected to respond to customer needs quickly. A slow response time can increase churn by 15%. Calendly allows customers to schedule meetings with the customer success employee via the company website or a support chat.

• Recruiters use Calendly to schedule more interviews with candidates and fill roles quicker. The tool helps increase initial screening calls and the number of qualified candidates and reduces the time to interview candidates. Calendly’s customers include Lyft, eBay, Dropbox, Okta, and more.

Market Size

Calendly operates in the global scheduling software market, valued at $393 million as of 2022. This market is expected to grow at a compounded annual growth rate of 9.7% over the next ten years, with North America predicted to grow faster than the global market.

However, Calendly has a different perspective on the market size, with multiple new hires estimating the true total addressable market for scheduling to be $20 billion, significantly higher than other estimates. One possible justification for this high estimate is that automated scheduling benefits a significant number of employees, regardless of the size of the business, industry, or geography.

Calendly operates in a market with various types of competitors. These competitors can be categorized into three groups: enterprise platforms (Google and Microsoft), functional platforms (HubSpot), and scheduling software companies (Doodle and Acuity Scheduling). Calendly holds an estimated 21% market share in the scheduling market as of 2022.

Scheduling Software

Doodle - Doodle is an online calendar tool for time management and coordinating meetings. It was founded in 2007. It was acquired by Swiss media giant Tamedia in 2014. While Doodle is pivoting toward the business space (especially with its 2022 visual rebrand), it was initially developed with the education and consumer audience in mind. Besides a more professional-looking user interface, Calendly offers features and controls you need for business scheduling and team management that Doodle just doesn't.

Acuity Scheduling - An online appointment scheduling software for businesses. Squarespace bought it in 2014. It focuses on small businesses in the service industry. Acuity requires more technical knowledge than Calendly. Acuity allows you to set up video meetings and sign documents effortlessly. Calendly will require additional software integrations for that capability.

YouCanBookMe - A tool for scheduling meetings and appointments, popular among universities and businesses in the education sector. It was founded in 2008 and is bootstrapped. For the growing company, YouCanBookMe may be the cheaper option because it gives you access to all of their tools starting with their $10 per month plan, while Calendly doesn’t unlock all features until you get to the $16 per month price point.

Chili Piper - Another meeting booking software player but geared towards revenue teams to help close more inbound leads. It was founded in 2016 and has raised over $50 million in funding.

Functional Platforms

Hubspot - A public company offering an online meeting scheduling tool in free and paid plans for its sales and marketing offerings. It is limited in what it offers and is designed to be a free tool that HubSpot offers its paid customers. This makes the platform affordable for businesses using HubSpot, but it is expensive at $50 per month Starter plan if you are not already using HubSpot.

Mailchimp - An intuit-owned email marketing company which offers tools to launch a website launch designed to take the hard work out of online appointment scheduling.

Enterprise Platforms

Microsoft - The enterprise productivity giant offers meeting scheduling through its Microsoft Booking, which integrates with Microsoft 365 and Teams. It only works with Office calendars, making Calendly a more flexible option for those using other calendar applications.

Google - Google also offers scheduling as a feature through Google Calendar. Unlike Google’s offering, Calendly works with all other calendars and integrates with tools outside the Google ecosystem.

Calendly operates a tiered pricing model to generate revenue, consisting of five different levels.

1. The "Basic" tier is free and designed for individual users, offering features such as connecting one calendar, one event type, and automated notifications.

2. The "Essentials" tier costs $8 per month per user, providing additional features such as connecting two calendars, unlimited event types, automated email reminders, and follow-ups.

3. The "Professional" tier, the company's most popular offering, costs $12 per month and includes collective event types, routing forms, analytics, customizable branding, and integrations with platforms such as Gmail, Outlook, and Hubspot.

4. The "Teams" tier costs $16 per month and offers additional features such as Salesforce integration and the ability to create round-robin events.

5. The "Enterprise" tier, pricing undisclosed, is tailored for teams with 30 or more members, featuring advanced security features and an account manager from Calendly.

Source: Calendly

Calendly leverages virality as its user growth strategy, utilizing a product-led growth (PLG) approach. A Calendly user shares a link to their landing page with potential meeting participants, and if the recipient finds the product valuable and time-saving, they may sign up and create their own landing page to share with others.

Source: Sacra

Calendly has experienced strong traction in recent years. The company says it's being used by over 10 million people and 50K companies worldwide. It has a global presence, with monthly active users in more than 155 countries.

200 million meetings have been scheduled using Calendly as of 2022. It reached $100 million in annual recurring revenue (ARR) as of 2021, showing a 43% growth rate from $70 million in 2020. This level of traction took the company just seven years to achieve from its initial $1 million ARR. It is profitable as of September 2022. The company acquired Prelude, a specialist in automating scheduling around job recruitment, in 2022.

Source: Sacra

Calendly announced it had raised $350 million at a post-money valuation of $3 billion from OpenView and ICONIQ Capital in January 2021. The funding was a milestone for Calendly, considering its previous funding round was a Seed round in 2014, where it raised $550K from Atlanta Ventures.

In 2021, Calendly's annual recurring revenue (ARR) was estimated at $100 million, implying a valuation of 30x ARR at the time of its funding round. However, as the company has not disclosed revenue figures or a growth rate for 2022, it is challenging to determine its current revenue multiple.

Calendly is an enterprise software tool with a seat-based model. Some similar companies include Workday, HubSpot, Salesforce, Monday.com, Asana, and Docusign. These larger public companies trade at a range of 3-6x NTM revenue. This could be used as a range for Calendly’s future valuation.

Source: Koyfin

Product Expansion

Calendly-owned Prelude helps organizations streamline their interview process from initial screening to the final rounds. Samsara, for example, was able to save 600 hours per year by using Prelude's software, which integrates into Applicant Tracking Systems (ATS) to track the interview lifecycle.

The long-term goal is to merge Prelude's software into Calendly, which will give the company a chance to become a leader in recruiting automation. Calendly can sell Prelude to its customers and pitch its software to Prelude's customers, which include Cloudflare, Samsara, and Duolingo.

It could take a similar M&A-driven approach to go deeper into other verticals. It has the opportunity to build or buy more workflows around its core scheduling experience to further integrate its software into the productivity stacks of its customers.

Calendly has already been building tooling not just for setting up calls with prospective customers but also for actively managing a sales pipeline, scheduling calls with new users, and onboarding. The company is getting deeper into functionality typically served by companies like HubSpot and Drift — sales, success, marketing, and recruiting workflows — via these kinds of vertical-specific features and 3rd-party integrations.

Source: Calendly

Enterprise Growth

Calendly, under the direction of CEO Tope Awotana, has set an ambitious goal of reaching $1 billion in annual revenue. Calendly has historically relied on bottom-up, word-of-mouth-driven self-service-based growth. While that works well with smaller companies, landing and retaining large customers with thousands of employees would require an enterprise-oriented sales, marketing, and account management machine. Stronger enterprise penetration means better retention and higher average revenue per user via more lucrative contracts. There’s also more opportunity to increase revenue from existing customers by selling to multiple departments or teams within a company.

Economic Downturn

The scheduling automation market is highly competitive, with players ranging from major enterprise productivity platforms like Microsoft and Google and functional vendors such as Hubspot and Drift. The big platforms can and do bundle scheduling as a feature in their core offerings and give it away for free or at very little cost. As enterprises re-evaluate their spending on software vendors to navigate the macro tailwinds, Calendly needs to demonstrate its value proposition to functional teams within companies.

Product Stagnation

Low barriers to entry and the high cost of customer acquisition erode Calendly’s product and growth over time. Calendly is going to have to move aggressively to make its offering stronger to keep large companies from replacing it with a bundled offering from other players or not giving it a chance in the first place. It faces a risk of being reduced to a feature that prospects expect from a larger offering versus a standalone platform that deserves to be used and paid for independently.

Calendly, a cloud-based scheduling automation platform, has established a user base of millions of people who benefit from its streamlined and user-friendly landing page, improving worker productivity. The company has expanded its offering with complementary features enhancing the meeting lifecycle. The growth and profitability of the company resulted in a $3 billion valuation in 2021. Moving forward, Calendly has the potential for growth by acquiring enterprise customers and integrating its recent acquisition of Prelude. However, the company faces competition from tech giants such as Microsoft, Google, and HubSpot, making it imperative to closely track the evolving features offered by its competitors in the future.