LinkSquares’ $161M growth strategy with Vishal Sunak

While going through your first round of funding after seed money can be exciting, many founders claim it’s a stressful experience—it’s fairly common for startups to go through numerous rejections before securing funds from an investor.

“We had about 60 to 70 rejections, we started running out of cash, [and] we were down to three or four paychecks,” says Vishal Sunak, founder and CEO of LinkSquares, one of the top legal software startups. “It was definitely a moment of stress, but we got through it.”

Several years down the line, LinkSquares raised $161M over five rounds of funding, cultivated a team of over 400 employees, and added hundreds of customers to the company portfolio. In this week’s episode, Sunak takes us through his journey building LinkSquares, how he navigated fundraising struggles, and the secret to unlocking growth.

Validate your product ideas before building

Sunak stresses the importance of verifying your product idea before building—a process only achievable through dialogue with potential customers. In LinkSquares’ case, the team devoted its initial year to discussions with legal leaders.

“[We talked] to a hundred leaders from the legal department before we [built] a software that could never work or sell,” Sunak recalls. This strategic move enabled the team to identify the correct pain points, paving the way for a viable and successful product.

Hire the right people

Sunak also stresses the importance of hiring the right people—especially sales leaders—and making sure they’re the right fit for the company. He explains that while it may be tempting to hire a sales leader that previously worked for a Fortune 500 company, day-to-day activities of a startup are very different from a corporation’s.

“You can’t hire a sales leader who has historically been selling $40M deals for a Fortune 500 and expect them to sell at a $30,000 price point for 30 days,” says Sunak. “They just operate very differently.”

The founder also shares a critical piece of advice when it comes to hiring the right person: “Pick someone [who] other folks earlier in their career journey will aspire to become.”

It only takes one investor

When it comes to rounds of funding—especially Series A funding—facing rejection is inevitable. Investors can say no for any number of reasons, from your go-to market strategy to your targeted buyers and more. These reasons don’t necessarily reflect the quality of your business idea, and sooner or later, someone is bound to notice what you’re offering.

“It just takes one or two people to see past the roughness and the edges, if there are any,” says Sunak. “You’ll know within the first 10 or 15 minutes if you’ve got chemistry with an investor or not.”