What is Calendly

Tope Awotona, founder and CEO of Calendly.


It’s been a crazy few weeks in tech, from Microsoft’s record $69 billion deal to buy Activision Blizzard to a frenzied series of earnings reports that saw Netflix and Facebook in panic territory, while that Amazon had its best rally since 2015.

Amid all the noise in the mega-caps, Twitter made sure that the smaller-dollar tech debates continued to rage with wildfire-like intensity.

Enter Calendly.

Calendly is a nine-year-old startup founded in Atlanta that runs a website where people show what times they’re available so others can book meetings with them. Its $3 billion private market valuation, according to PitchBook, is new in the decacorn era.

As the recipient of a Calendly link, you open a website with a calendar, select a day, view available times, and “confirm” a time slot. Then you enter your contact information and Calendly will generate an invitation that will appear on both attendees’ calendars.

The rather innocuous app became the center of a searing controversy late last month, after Silicon Valley entrepreneur and investor Sam Lessin posted a tweet criticizing the people who use it.

“When someone sends you a Calendly link and asks you to sign up on their calendar, they’re telling you that you’re less important than them/and that ALL of their ongoing meetings are ‘more important’ than whatever you’re doing. need them – it’s an ‘online’ movement,” Lessin wrote.

Dissenters have loudly proclaimed that he takes things too personally. Supporters of Lessin’s tweet were grateful that someone was finally standing up for the masses. One person tweeted that requesting a meeting for advice and then sending a Calendly that is only open during regular business hours is “rude as hell.”

Thousands of people posted opinions on Lessin’s post. Some of them were flattering; a lot could be considered deflating.

Tope Awotona, founder and CEO of Calendly, has taken the approach that all attention is good attention. On Twitter, he said he was enjoying “a huge spike in signups” and offered an extra dig, thanking Lessin “for all of his portfolio of cos who rely on Calendly to win and delight customers.”

Patrick Moran, chief marketing officer of Calendly, spoke to CNBC last week about the immediate consequences of a random event in the company’s history. (A company spokesperson said the CEO’s schedule was booked.)

User growth has increased, Moran said, and not just free users. Paid businesses also signed up, which kept Calendly’s chief revenue officer busy.

“Let’s just say our current CRO is super excited about the incoming demand that’s been created by some pretty notable names,” Moran said.

Calendly has more than 10 million users and says its enterprise customers include software companies like Asana and Okta. It’s a product that gets a lot of free exposure because people get Calendly invites from people in their network who want to host a meeting. That’s why Lessin knows so much.

Awotona decided to start Calendly based on his own experience working in sales, and he used his savings and retirement funds to get the business started.

“I was looking to schedule a meeting one day, and it took way too many emails to do it, and I got frustrated,” he said in a video from 2019.

Play well with others

When creating a Calendly account, users can choose to sign in Apple, Google or Microsoft calendars to avoid the risk of being double booked. Users specify when they want to accept meetings and can then send the link instead to find a mutually agreeable time with another person. Meetings can be customized for duration and can include options for video like Zoom.

Moran says the software helps bridge the gap in a world with many different calendar apps.

“They don’t necessarily play well with others and aren’t designed to be able to see through, and that’s where Calendly lives,” Moran said.

In addition to offering a free service, Calendly offers a premium version starting at $8 per person per month, and tiers for teams are also available. The company reported recurring subscription revenue in 2020 surpassed $70 million.

There is strong competition in the market. Google has rolled out appointment booking features for paid accounts. Microsoft takes a slightly different approach with an Outlook add-in called FindTime, while LinkedIn’s paid Recruiter service also includes Calendly-like functionality.

“They both tried to do it, and they just did a shitty job,” said Tim Campos, who sold calendar app Woven to Slack last year for undisclosed terms. Lessin was an investor in Woven, which had its own component called scheduling links, allowing users to suggest specific available times.

Campos kept a close eye on Calendly. He wouldn’t use it to host board meetings or parties with his wife, but he said it became applicable in many other scenarios.

Between in-house sales departments and independent consultants, “there are enough that this market alone could easily justify several hundred million dollars in revenue per year,” Campos said.

As for Lessin’s view, Campos said it “applies to a subset of the market.”

Andreessen Horowitz Partner Marc Andreessen

Justin Sullivan | Getty Images

Lessin, who was vice president of Facebook until 2014 and is now a partner at Slow Ventures, has a decent but not huge following on Twitter.

Marc Andreessen, meanwhile, is a dominant figure in Silicon Valley and has over 900,000 Twitter followers. He jumped into the conversation with a touch of humor.

“Notice effective immediately: Anyone who disregards my Calendly connections will be permanently banned from raising venture capital in Silicon Valley,” Andreessen wrote.

When Moran saw Andreessen’s tweet at the top of his feed, he knew the discussion had reached another level.

“I was trying to figure out what he was saying without reading all the comments in between,” Moran said.

It was like a trader’s dream, Moran said. And, he added, while there was a lot of noise to sift through, the company was able to draw out some helpful suggestions on how to make the product more user-friendly for bored recipients.

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