CalendarHero parlays successful pivot into potent acquisition by Vendasta

Every startup is a complicated journey, and CalendarHero’s was seven years, including a name change and a pivot, but it’s that specific fork in the road that led founder Roy Pereira to exit.

On October 26, Vendasta announced that it had acquired CalendarHero – formerly known as

Responding to a comment that the acquisition must be welcome news, Roy Pereira, founder of CalenderHero, said: “Better than I could expect, I must say.”

“We went deep, and that’s basically why we’re here.”
– Roy Pereira, founder of CalenderHero

CalendarHero offers AI-powered automated scheduling software, while Vendasta provides an end-to-end platform for companies selling digital solutions to local businesses.

The terms of the deal, which closed October 15, were not disclosed.

CalendarHero will retain its employees, and the startup has already joined Vendasta’s Owned and Operated SMB division, which produces products for SMB clients. A full Vendasta platform integration is in development that will allow CalendarHero functionalities to work with Vendasta’s existing CRM. Pereira becomes Vendasta’s new general manager.

“I just find the synergy between the two companies within tech, and how we approach markets is really great,” Pereira said. “But also the culture fit. If anyone knows me I’m really big on work-life balance and work environment and culture, and really pleasantly surprised to find the same in the Vendasta culture.”

The two companies came across each other when CalendarHero was investigating the possibility of getting into Vendasta’s app marketplace because of its large distribution network. “That’s when we started talking, and of course history is history,” Pereira said. “We’re here today.”

Getting to this point wasn’t so easy. The startup began in 2016 as with a vision of offering a personal AI assistant to employees, one that automates menial tasks such as meeting scheduling, flight searches, internal document searches, and reminders.

Pereira told BetaKit in December 2018, after raised two rounds of financing (a seed round in 2017 and a seed extension in 2018) and completed an acquisition, the leadership team noticed the business was not hitting certain success milestones with regards to product-market fit.

As Pereira tells it, the market wasn’t ready for an executive assistant that was a bot, and that you spoke to in natural language. “That was maybe a bridge too far for a lot of people. And I know the market isn’t even quite there today,” he said.

So in 2019, pivoted to focus on scheduling software. Not everyone at the company liked the idea; more than half the team left.

That didn’t deter Pereira. The startup looked at its data, examined the market, conducted a lot of user interviews, and figured out scheduling was the feature everyone wanted. “We went deep, and that’s basically why we’re here,” Pereira noted.

He claimed the company experienced a five times increase in product usage, finally achieving the product-market fit had been seeking. “The functionality we had in the product made sense to people, and people were using it,” Pereira said.

In March, the company changed its name to CalendarHero to better reflect its business and product.

RELATED: Vendasta secures $119.5 million in venture funding after pausing IPO plans

Up until its acquisition, CalendarHero had raised just slightly less than $6 million CAD. With the acquisition, all the investors have exited the 11-person company.

The acquisition brings Vendasta to a total of about 575 people, and adds 100,000 existing CalendarHero users to the integrated company.

Founded in 2008, Vendasta offers a cloud-based commerce software and app marketplace for companies that provide digital products and services to SMBs. The startup pulled in revenues of $42.6 million in 2020 and $34.5 million in 2019.

Vedasta most recently raised $119.5 million in venture funding in May after shelving plans for an IPO in March when the market cooled down. It was the largest information and communication technology venture capital round in Canadian Prairie history. Vendasta is evaluating other acquisitions in support of growth plans set in motion by the financing round.

“We’re here to help our partners and their small business clients thrive,” said Brendan King, co-founder and CEO of Vendasta. We have a set of foundational products that every local business needs: Reputation, listings, social media management and websites. Much like those solutions, every business needs a calendar. CalendarHero is best-in-class, and we’re very excited to have them here as part of our platform.”

Pereira claimed that in the last few months CalendarHero has doubled revenue. “Of course that will continue, and be accelerated by the Vendasta deal,” he said.

“Vendasta has been a rocketship lately with its funding of $120 million.” Pereira added.”I think it’s a really interesting time to see the Canadian tech scene produce these unicorns, and these very fast rising rocket ships, and that’s what I’m excited about.”

Charles Mandel

Charles Mandel

Charles Mandel's reporting and writing on technology has appeared in, Canadian Business, Report on Business Magazine, Canada's National Observer, The Globe and Mail, and the National Post, among many others. He lives off-grid in Nova Scotia.

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