Squire's Kevin Cheney among locals betting their careers on early-stage startups – Buffalo Business First

With the success of ACV Auctions, Buffalo now has breathing examples of early startup employees who saw near-worthless shares turn into ownership stakes worth hundreds of thousands, if not millions.
This is the deal: A startup pays you with shares to make up for the salary you’re forgoing.
If the company goes belly-up, so does your bet.
If they hit, then there are few better ways in the world to generate rapid wealth.
Buffalo Inno has been chronicling employees at other companies who are the cusp of such success.
The St. Joseph Collegiate Institute and Canisius College graduate was at Shea’s Performing Arts Center on Oct. 6, 2017, for the finale of that year’s 43North business competition.
He watched Squire co-founder Songe LaRon and Dave Salvant describe how their firm was positioned to become the technology partner behind an overlooked-but-massive niche: independent barbershops. At work in the following days, he watched the pitch again. Then he emailed LaRon and told them he could help.
“I knew I needed a company that would let me punch above my weight, because I did not think my resume was a good barometer for my ability,” he said. “They took a shot on me.”
Cheney became Squire’s first employee in Buffalo on Valentine’s Day in 2018, when he started as a customer success agent. He was Squire’s seventh employee overall.
What happened next was a whirlwind, and that’s probably underselling it.
Squire – officially headquartered in New York City and with employee hubs in Texas and Toronto – recently closed on a $60 million round of venture capital at a $750 million valuation. The company has more than 20 employees in Buffalo and more than 200 overall and a roster of celebrity and executive investors – M&T Bank CEO Rene Jones cut a check in 2020. Because of its initial investment, 43North is a significant shareholder.
Cheney declined to discuss the details of his compensation, but there’s no doubt he landed on the right side of an early-stage company.
He is now the onboarding manager, reporting to the company’s vice president of operations, and leading a team that helps new Squire customers implement and use the software.
The best thing about a company like Squire — which has hit continuous growth spurts as its business has grown expansively, supporting by a significant amount of venture capital — is the opportunity to build something unique, he said.
“What excites me most, when I look back even six months ago, is that I hardly even recognize my role,” he said. “The only thing that’s stayed the same is that this is a company that prioritizes hustle – we hustle for our accounts and for our customers and it’s really, really fun.”
Cheney said that working at a company like Squire requires an appetite for solving big challenges – they never stop coming. The company has to manage its fast-growing operations while continuing to prove that it can successfully acquire customers and keep them happy, which is a lot to handle when its overall goals are expansive international growth. There are new products to develop and revenue-bearing segments to watch over, from monthly subscriptions to transaction fees.
“There are some days when Squire is a deep, deep challenge,” Cheney said. “I’ve learned a lot from the many situations I’ve been exposed to at Squire.”
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