In the summer of 2019, Chris Ake and a couple of fellow tech entrepreneurs entertained the idea of building out artificial intelligence-fueled smart scheduling software they were already using to quickly and easily schedule meetings.
When the trio was finally ready to launch the first version of the software called Sidekick, the concept of business meetings had shifted drastically.
“I made a joke back then: ‘It was just my luck that we’re going to launch a software project that helps schedule meetings with people and the world shuts down,’” laughed Ake, CEO of Sidekick Ai.
Like so many other businesses that saw visions for 2020 rocked by the COVID-19 pandemic, the Sidekick Ai team — which also includes founder/partner duo Jon Butler and Nathan Jean — had to sift through the chaos to find opportunity.
Despite the sudden extinction of in-person meetings, Ake and his team realized the era of digital meetings could benefit even more from a product like Sidekick, which utilizes machine learning as one way of scheduling meetings with clients and co-workers.
“It kind of opened my eyes. People are always going to have to meet and connect, but the method might change,” Ake said.
Sidekick offers several ways to schedule meetings. One of the primary avenues is through forwarding emails to Sidekick that contain either requests to meet or specific meeting information, such as date, time and location.
Through machine learning, Sidekick scans the email, processes the language and either responds with potential times to meet or sends an invite for a meeting.
A user can also schedule meetings with others through Sidekick with a shareable link, by chatting with Sidekick or by setting auto scheduling, which allows specified users to schedule meetings directly without additional approval steps.
The software can be integrated with Gmail, Google Calendar, Outlook, Outlook Calendar and Hangout. A Zoom integration is on its way, according to Ake.
The Sidekick team has bootstrapped the project thus far. Ake and Butler founded Grand Apps in 2011, a Grand Rapids-based web application development firm. Two years ago, the duo joined Jean at Kyros Digital LLC, which specializes in custom software and mobile apps.
The Kyros team has developed Sidekick as a side project, and Ake hopes the new company can soon hire two full-time developers of its own to focus solely on Sidekick.
Sidekick started with around 100 beta users — friends and colleagues — and it now has 350 users on its platform, fueled by their listing on AppSumo, a directory of apps and software for entrepreneurs. Sidekick has processed around 150,000 emails through its forward to schedule feature.
“Our product kind of markets itself — once you get up to the 5,000 mark (for users), the numbers start to get pretty good, even with a pretty conservative conversion rate,” Ake said. “So (5,000 users) is our north star.”
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