How Calendly went from a meme to a must-have business tool

Calendar scheduling tool Calendly says it’s in a unique position to grow despite the cash crunch for startups.
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Hannah Minn

· 5 min read

What do you do when your company has been meme-fied? Its brand solidified for the internet, Calendly found itself in that position, often seen as the scheduling app for venture capitalists who tell eager founders and even more desperate students to get in touch! by booking calendar time.

Calendly is trying to change its image as an individual user tool, finance chief John McCauley told CFO Brew, to that of an enterprise one. But the days of endless growth (we miss you, 2021!) seem like they are also in the past, so companies like Calendly are tasked with growing a startup without running out of cash cushion. Enter the CFO.

“Enterprise is the fastest growing part of our business today,” McCauley told CFO Brew. He said the company’s customers who spend more than $100k per year on Calendly have increased 100% YoY. McCauley pointed to a key customer, Asana, which has implemented Calendly internally: “We’ve seen Asana schedule more than 36,000 meetings and save over 9,000 hours.”

While many CFOs may have a tight runway, McCauley told CFO Brew that the company is not going to hide from the macro environment. “The opportunity is massive, and we’re just getting started,” he said.

Calendly was launched in 2013 by Tope Awotona, an immigrant entrepreneur from Nigeria who gathered $550,000, including his life savings, to get the SaaS startup off the ground. Awotona started the company after personally struggling to swap schedules to find meeting times with coworkers—a modern headache. The company raised $350 million in January 2021, bringing its valuation to $3 billion.

In the years since its founding, the scheduling tool—and the overall etiquette of inviting someone else to find time on your calendar—became a buzzy topic of conversation. Calendly has posted to its own blog to clarify how to use the platform in a non-triggering way, with posts detailing how to send links politely and claiming that scheduling has become more socially acceptable over time.

Tough startup market. In the current moment, startups like Calendly are looking at tighter market conditions, and some say the squeeze could lead to increased company sales (at lower values) and to giving up more equity to investors. Others are looking toward alternative funding methods to avoid these measures; after all, cash is still king.

Blake Bartlett, a partner at venture capital firm OpenView, told CFO Brew that while SaaS companies are here to stay, customers may be looking at their tech stack more closely for where to cut and what must stay.

“The CFO has come into the picture, more so than ever before,” Bartlett said. “And saying, ‘OK, great, prove the business value to me, show me the business case.’ It’s basically like fewer things get a yes on the new budget.” That could be trickling into the SaaS sector as fewer budget dollars are flowing, Bartlett added.

Global venture funding fell 66.7% YoY in December 2022, according to S&P Global Market Intelligence data. Comparing December 2021 to December 2022, funding rounds clocked in at 1,104 versus 2,545 for the former.

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McCauley said that the main draw for him to join Calendly was the company’s plan to scale to enterprise level. The finance chief joined the firm in June of 2022, giving him a little over six months on the job.

Growing by acquisition. Last fall, the calendar company acquired Prelude, a recruitment scheduling platform, that will likely be absorbed into its tech stack. The founder of Prelude, Will Laufer, shifted into a role at Calendly as the head of sales, recruiting solution. And, if hiring is any sign of a company's health, Calendly appears to be still recruiting.

The Prelude acquisition is one piece of the enterprise growth the company told CFO Brew it’s planning, which includes tapping into recruiting and sales teams. “We’re also thinking deeply about this across departmental use cases, like sales and how we support the evolution of the sales process from being that of an art to that of a science with a platform like Calendly,” McCauley said.

The company also pivoted to being fully remote since 2021 after adding 200 employees since the start of the pandemic, which seems to align with their goal of connecting teams who are dealing with hectic schedules to chit chat about calendars.

“We’re moving into a territory where we don’t have a lot of data, we don’t have a lot of DNA built into the organization that is good at selling into large enterprises,” McCauley told CFO Brew. “But that’s where we find ourselves, and we’re starting to do remarkably well. And as part of that, there’s a lot of creativity built in and how we decide to define this business again.”

Keeping an eye on competitors. As with any company, it isn’t the only offering on the market; competitor raised $25 million in a funding round last year. Google also is said to be spotted rolling out features that rival Calendly’s core products.

So, how do these numbers add up? While Calendly is a privately held company, it’s harder to peek into their finances, but McCauley said that the company has always been an “outlier in terms of fast growth and disciplined profitable management.”

McCauley said he was “hesitant” to say the company was reinventing itself. “We’re going to still be great at that PLG [individual offering], but it’s an augmentation that requires a lot of creative thinking, and that’s a huge focus for us,” he said.

Bartlett, an investor since 2017, said when the scheduling platform announced it had raised an additional $350 million in 2021, the VC firm was sold on the platform’s vision of scaling from an individual product to then a teams product and then the next phase: an enterprise product.

“It’s like you join a new company, in a new job; you get your computer, you get your Slack, you get your email, you get your Zoom account, and get your Calendly. They count it as sort of a standard thing for basically all knowledge workers today.”—KT

News built for finance pros

CFO Brew helps finance pros navigate their roles with insights into risk management, compliance, and strategy through our newsletter, virtual events, and digital guides.