If you do any type of online communication, chances are you’ve had a Calendly link thrown in at you at some point.
Maybe you even use it yourself.
Calendly is the fastest-growing company in the scheduling automation niche, and they hold 12.13% of the market share in the space (up from 8.35% in 2019).
As of 2020, Calendly is serving over 5 million active monthly users (up from ~4 million in 2019).
The company was launched in 2013 by Nigerian-born CEO Tope Awotona, and has since then seen continuous growth in annual revenue.
Awotona has started out his work life doing jobs in sales during college. His experiences ranged from cold calling for donations at a non-profit call center to selling alarm systems door-to-door for ADT.
The experiences helped Awotona kick-start a 7-year career in enterprise software sales, working for the likes of IBM and Dell EMC, all while dabbling through building three start-ups: a dating website, projector e-commerce store, and a platform for selling home equipment—though none of which have generated any profits.
Working full-time in sales, Awotona has grown frustrated with the long email exchanges leading to setting up calls with prospects. This has led him to a six-month journey of research for a product that would solve his problem.
Coming out empty-handed from his research, Tope spent six months analyzing the strengths and weaknesses of existing scheduling automation tools and ended up getting a flight ticket to Kyiv, Ukraine. There he started working with Railsware—a software development company—and sowed the seeds of a $60 million SaaS; Calendly.
Six months and $200K later, Awotona launched Calendly’s MVP (Minimum Viable Product) in 2013, and he never looked back since.
How Calendly Attracted Their First 1000 Customers (2013)
Calendly’s Top 3 Success Elements
Having studied competition before launching the product, Calendly had to focus on three elements to stand out:
1- Reduce the steps it takes to schedule a meeting using the tool (i.e. seamless UX and elimination of time zone related issues)
2- Simplify design functionally and aesthetically
3- Maximize integrations and facilitate their use
With these problems solved, the next challenge for Calendly was to get their product out there.
And given the nature of the SaaS, that was not the biggest challenge Calendly faced.
Using Calendly dictates sharing “calendly.com” links with outside parties, which automatically introduces them to the product without any advertisement or marketing costs for Calendly.
It is a hybrid product, in the sense that it serves B2B and B2C users alike. Add this to the inherent virality of the product and you get an infinite pool of users.
Calendly’s #1 Marketing Strategy: The Upside Down Funnel
Knowing the nature of their product, Calendly focused their efforts on giving their existing users the best experience. They like to name this strategy “flipping the funnel upside down”.
What that means is that their biggest focus was not acquiring users, but rather keeping them.
This has helped Calendly rely less on paid advertising methods that would have required raising a lot of VC (Venture Capital) and caused the company to have less financial and directorial control.
Calendly’s First 1,000 Users
The first Calendly users were members of a company in the Bay Area called BrightBites. After a discussion with Calendly’s CEO about his product, they started using the MVP (Minimum Viable Product) before launch.
And since BrightBites worked with educational institutions, it was not long before a school sign up for Calendly and started using it for parent-teacher meetings.
The biggest turning point that enabled Calendly to reach their first 1,000 users was when the school reached out to Calendly and wanted to roll out the product to 80 people.
Calendly listened and made it possible for individual accounts to invite team members.
Quickly, those teams grew into departments, and more users introduced Calendly to outside parties and helped Calendly reach their first 1,000 users.
The Best Decision Calendly Did NOT Make
Up until July 2014, Calendly was totally free, as CEO Tope Awotona did not have enough capital to pay the development team to create website payment plans.
Surprisingly, that turned out to be what Awotona calls ‘the biggest decision Calendly did not make’, as making all features available to users for free helped the company spread like wildfire.
The company was founded in 2013, and initially raised a seed round from InkWell around the end of 2013, and to develop monetization features, Calendly had to raise another round on the 25th of April 2014 amounting to $550K from Atlanta Ventures.
And that’s where Calendly started making money.
Making Calendly a Business: Growing From $0 to $100K in ARR (Annual Recurring Revenue) (2014)
Striking a Balance Between Paid and Free Plans
After one year of not making a penny, Calendly received enough funding to continue product development and started experimenting with several payment plans and packages in July 2014.
They had to strike a balance between a free plan that would keep users coming in, and paid plans that would make sense and get income.
Calendly tested several price points for different packages, ranging from $5 to $10 monthly per user, and ended up sticking to a free plan and a premium plan at $8/month billed annually or $10/month billed monthly. Plus, they had a 14-day premium plan trial option available for all new users.
The main features that Calendly monetized at this point were automated reminders, Calendly branding removal (Powered by Calendly), and personalized notifications.
Instead of grandfathering existing users, Calendly downgraded everyone to their new freemium plan and offered their new paid packages. Nonetheless, CEO Tope Awotona says if he had to do it again, he would upgrade existing users instead, as they have had some unhappy customer complaints as a result of that decision.
An Average Increase of $25K in ARR (Annual Run Rate) 4 Months After Monetizing Calendly
This has enabled Calendly to generate their first $100K in only four months, averaging a monthly increase of $25K in ARR (Annual Run Rate).
At this point (end of 2014), Calendly was making no profit and still was not able to cover their existing costs.
But since they had VC (Venture Capital), were making money, and had low CAC (Customer Acquisition Cost), Calendly was moving in the right direction.
Reaching Profitability: $100K to $1M in ARR (2015)
Flexibility and Adapting to Customer Needs
One great factor for Calendly’s success in making their first $100K is their adaptation and flexibility throughout the company’s journey.
With customer experience being a priority, Calendly invested their resources into fulfilling their customers’ requests and reducing friction points within the SaaS. They even based their segmentation on users’ behaviors and requests.
But what made Calendly get to profitability and make their first $100K was automation. The company had to make purchasing, upgrades, and switching plans even easier for accounts.
For example, many team managers wanted to pay for new team members working offline and include them in one account, which is a pretty narrow request.
After watching many of these clients drop off when their requests weren’t met, Calendly had to create solutions to fulfill those special requests.
Because they did not have enough manpower to integrate new features overnight, they had to start sending manual credit card forms to collect payments, which was a good enough solution to keep those customers around.
Revamping the Design to Meet Market Standards
With the rise of Apple as one of the biggest companies by market cap, their seamless, easy-to-use UX (User Experience) set a standard in the market and forced hardware and software companies alike to develop newer platforms.
Calendly had to get on that wave in 2015, and they’ve totally revamped their website, logos, and scheduling tool design.
Here are screenshots of their $100K and $1M homepages respectively:
Before (end of 2014):
After (End of 2015):
Here is another before and after of their scheduling tool:
Making Premium Plans Even More Appealing
Initially, the premium plan at Calendly did not offer a lot more value compared to the free plan. Few were the extra features, and people mostly wanted to upgrade for only a feature or two.
To wrap up 2015 with a blast, Calendly had to continuously keep adding premium features to their paid plans to make it an even more appealing option.
They’ve added around ten premium features: group event scheduling, reporting, customizable event reminders, and more.
And given the importance of teams to Calendly’s growth, they have gone the extra mile to offer special discounts for teams of five or more people.
These changes have contributed to taking Calendly from $25K to $75K in average monthly increase in ARR (Annual Run Rate), which brought the company to profitability and $1M in annual revenue.
From B2C to B2B: $1M to $4M in ARR (2016)
Automating the Customer Journey
After hitting the one million dollar milestone, Calendly had no option but to start following a low-touch sales model. The number of enterprise clients was increasing drastically against other segments, and the budget those companies had was all Calendly needed to hit their next revenue goals.
At this phase, the company had to start hiring new people to fulfill users’ needs, but in a different way than the previous years.
Instead of dealing with every problem independently and having to dedicate custom credit card forms and support to users, Calendly hired manpower to go full-on automated and decrease their users’ interactions with customer success in the future.
They needed to automate all life cycles for different segments, ranging from K-12’s to small teams to large corporations.
Team Scheduling and Administration
With the increasing demand from corporations’ sales teams, many features for this segment had to be developed by Calendly’s team.
When it comes to online scheduling, there are several not-so-productive tasks that suck up sales reps’ energy and time. Calendly has added two new features to address that:
- Combining team members’ availability (to share only one schedule with customers)
- Automated meeting distribution among sales teams
Administrator capabilities are another key element Calendly focused on at this phase. Admins were allowed to manage their teams on the platform, but allowing them to add and remove users, manage permissions, and more.
Enabling these features resulted in making users’ scheduling experience more efficient and less reliant on Calendly’s success team.
To maximize revenue, Calendly had to always make the premium option more appealing. They had to keep giving users reasons to buy.
That is why they ended up developing integrations with tools such as Salesforce, GoToMeeting, and Zapier.
Moreover, they have enabled API integrations for companies to streamline functions and make Calendly easier to use across multiple cloud-based apps.
Plus, they have made auto code generators available for users to embed Calendly pages on their websites and get calls scheduled without having to send prospects to a new page.
Recruiting an Inbound Sales Team
In addition to recruiting new employees for product development, Calendly found itself in a need to hire a sales team.
More and more big sales teams and corporations were signing up, some with 300+ team members.
The process for signing up and onboarding the whole team was automated, but those companies needed help with change management.
Calendly’s new inbound sales team was tasked to help those teams adapt to using a new product and integrate it with their existing work processes.
Accepting Purchase Orders
Initially, Calendly only accepted upfront and online credit card payments. With the emerging new segment of corporations, a new payment method needed to be introduced—purchase orders.
Purchase orders allow companies to track and control expenses on outsourced products. Making this possible for Calendly users made the scheduling tool an even more appealing option to corporations.
Adding the above adjustments and integrations to Calendly and hiring 25 more employees throughout 2016 helped grow the company’s portfolio and attract top brands such as Marketo, Zendesk, Uber, and others.
Taking Calendly From $4M to $10M in ARR (2017)
New Billing Plan to Maximize Revenue
By the start of 2017, Calendly realized they have a segment of companies that work with big budgets. This segment dominantly consists of companies that use Salesforce.
Therefore, Calendly came up with a new “Pro” plan that is priced higher than their
“Premium” plan. At $12 a month (billed annually, or $15 billed monthly) for the “Pro” plan, Calendly offered all “Premium” plan features plus Salesforce (which was removed from the “Premium” plan).
Billing plans in 2016:
Billing plans in 2017:
Calendly attracted a variety of segments to use their tool. Yet, up until 2017, they did not position themselves to tangibly appeal to the needs of every segment.
Realizing how much business they could be missing out on due to poor positioning, Calendly hired dedicated product managers for each segment and started to roll out even more features.
In addition, they created different case studies to demonstrate the different use cases of Calendly.
Here is an example of a case study for Calendly’s K-12 segment:
And to make their positioning even more present, Calendly trained their customer success team to tackle different segments in a personalized manner.
At this point, Calendly had ten customer segments that covered their whole clientele.
By the end of 2017, Calendly had more than 50 employees, averaged a $500K monthly increase in ARR, and ended up making $10M in revenue.
Growing Calendly From $10M to $60M in ARR (2018-2020)
New Features & Segments
After hitting $10M in revenue, Calendly maintained a very stable pace. The main changes they applied concerned their features and segments.
Calendly shrunk down its segments from ten to six in 2018. And to this day (2020), they are still targeting and working with the same segments.
When it comes to features, they added numerous integrations to make their $12 “Pro” option even more attractive. That includes HubSpot, Facebook Pixel, Microsoft Teams, Intercom, Zapier, PayPal, Zoom, Mailchimp, and more.
Instead of having only one reason to upgrade to the “Pro” plan (which was the case in 2017 with Salesforce), Calendly users now can benefit from many more features (and counting) at the same prices.
In addition, although Calendly does still not rely on outbound sales, they have stepped up their social media game. Around the start of 2020, Calendly created a YouTube channel and started using LinkedIn to promote their brand to professionals.
Calendly & COVID-19
Starting from March 2020, COVID-19 dominated media headlines and countries started forcing movement restrictions. Consequently, consumer behavior has changed dramatically, and this affected all businesses both negatively and positively, including SaaS.
Online work went from a “nice to have” perk to an obligation many companies and schools had to adhere to. Consequently, online meetings became more prominent than ever, which created a big need for an efficient scheduling tool.
Calendly has benefited greatly from these changes. In fact, Calendly meetings held via Zoom went up by 715% since the outbreak of the pandemic, and more than 60 million meetings have been scheduled using Calendly during the same time period.
Seed Round Investment in November 2020
Calendly’s continuous growth was rewarded when OpenView (a venture capital firm) decided to invest a sum of $550K into Calendly’s expansion on the 17th of November 2020.
Less than three months later, the same firm comes in with a much bigger sum of cash that put Calendly at a whopping $3 billion dollar valuation…
Calendly Raises a $350M Investment in 2021
With Calendly’s fast growth during the pandemic, venture capital firm OpenView had to jump in on the growth wave. Along with Iconiq Capital, they have led the round to raise a $350M investment; which put Calendly at a $3B valuation as of the 25th of January 2021.
This round is aimed towards providing enough liquidity for Calendly employees and early shareholders, as well as hiring new executives for senior positions to grow Calendly’s team and products.
Calendly’s CEO Tope Awotona has not initially recognized a need for such an investment as he deemed it as a “distraction”, but his explanation for taking on this round was OpenView’s and Iconiq’s extensive experience in the tech space.
After crossing $60M in revenue in 2020, Awotona says in a recent announcement that he is setting his sights on hitting $1 billion in annual revenue.
Here are a few things you can learn from Calendly:
Keep your costs low. Outsourcing the development of Calendly to a country with a cheaper cost of living (Ukraine) made it more affordable for the CEO to bootstrap the company without relying on outside investment.
Focus on the first 1,000 customers. As stated previously, the best decision Calendly “did not make” was making their product totally free for the first year. If you are running a B2C or a low-ticket SaaS model, focus on getting that first batch of customers at a low or no cost before starting to make a profit.
Customer is king. Calendly’s MVP was best fit for individuals. But, as demand arose from other segments like SMBs (Small to Medium Businesses) and corporations, Calendly adjusted accordingly to match those needs. The company never imposed its will on customers.
- $0.1M in ARR 2014 – CEO Presentation
- $1M in ARR 2015 – CEO Presentation
- $4.1M in ARR 2016 – CEO Presentation
- $10M in ARR 2017 – CEO Presentation
- – 2018
- $30M in ARR 2019 – The SaaS Podcast
- $60M in ARR 2020 – GetLatka
- 3 in 2014 – Calendly (Archive.org)
- 5 in 2015 – Calendly (Archive.org)
- 30 in 2016 – Calendly (Archive.org)
- 50+ in 2017 – CEO Presentation
- 24 in 2018 – Calendly.com
- 82 in 2019 – Calendly.com
- 211 in 2020 – LinkedIn
- – 2013
- – 2014
- 120K active monthly users in 2015 – Railsware
- – 2016
- 1M active monthly users in 2017 – Calendly (Archive.org)
- 2M active monthly users in 2018 – Calendly (Archive.org)
- 4M active monthly users in 2019 – The SaaS Podcast
- 5M active monthly users in 2020 – Calendly.com
Source: Calendly (Archive.org)
April 25, 2014
OpenView & Atlanta Ventures
Source: Owler, The Business Journals
November 17, 2020
OpenView & Iconiq Capital
$350M (Private Equity Round)
January 25, 2021
Author: Yassir Sahnoun
Yassir Sahnoun is a content strategist and writer for SaaS companies. He specialized in generating leads using long-form content. His portfolio includes top SaaS brands such as CrazyEgg, Document360, and SitePoint. You can connect with him on LinkedIn or visit his website yassirsahnoun.com.