LinkSquares was buzzing. The contract management platform had its seed round in 2018 and had tripled its revenue when it set about its Series A, and things briefly got dicey, as Co-Founder and Chief Executive Officer Vishal Sunak recalled on a 2023 podcast. “I really think Series A, probably the hardest one there is,” he said. “You’re kind of like an awkward teenager. You’re not quite a full-blown adult, but you’re not like just an idea with a bunch of people.”
Sunak kept plugging away until the raise was done, but the experience stayed with him. “You know, maybe 60, 70 rejections, starting to run out of cash, then thereafter, getting down to three, four payrolls, and then kind of having the belief that we would get it done and go get it done,” he said. “That was definitely a little moment in some of the maybe more stressful 100 days of my life. But we got through it.”
It was a pivotal moment for the Northeastern University graduate, and since then, LinkSquares has grown to the point that, like many companies these days, it recently introduced an artificial intelligence assistant to help its customers navigate the often messy world of contracts. Powered by LinkAI, the autonomous agent helps with proactive renewal management, portfolio management, and compliance oversight, leaving more time for executives like Sunak to further advance the rest of the business.
The goal is simple: to make contracts easier. It’s the company’s founding principle—the one that led to those awkward but fruitful funding talks so many years ago. “My co-founder and I had that direct pain working at a company that got bought by another company,” said Sunak. “And the big company that bought us asked us what was in all our contracts. So it was like, dang, hey, this is interesting. Like, why is this so hard?”
From that moment on, Sunak set out on a mission to make sure it wouldn’t be hard, honing his natural sales abilities. “I think it’s a mandatory superpower… all founders have to be able to sell at some level,” he said. He set out on the path he continues to walk to this day, far removed from his Series A jitters. The company has raised more than $160 million and counting. That’s a lot of success, and a lot of contracts—and there are always more to come.