Saile closes $1.35M round; set to double team in 2023 as mass production of ‘robots for salespeople’ under way 

A Kansas City startup building an army of “Sailebots” — an artificial intelligence solution to a classic industry problem — impressed its new lead investor with its customized approach that avoids a “one size fits all” strategy. 

“I’ve been in sales and marketing automation for 20 years,” said Lisa Calhoun, founder and managing partner at Atlanta-based Valor Ventures, which led a $1.35 million seed round for Saile.ai. “[Saile] automates one of the toughest frontiers major companies have today — prospecting.”

Through the technology, Nick Smith is on a mission to build a world-class company, he said. Robots for salespeople, or Sailebots, are personality-driven AI technologies that generate actionable revenue opportunities, as well as read and react to text, said Smith, who co-founded Saile alongside Clive Cadogan in 2018.  

“Not only is our technology proven to grow with clients, but it’s our main growth driver. We’ve built an ecosystem around this patent-pending technology. That is what’s so interesting and scalable about Saile,” he said. 

Click here to read more about why Nick Smith founded Saile.

KCRise Fund, a Kansas City-based venture capital firm, also signed on to Saile’s seed round; Saile is the first investment out of KCRise’s Fund III, Smith said — adding that he and his team were intentional about having a local investor. 

“Given the macroeconomic environment, or climate, we’ve been a conservatively managed company that’s tried to shoot for cash flow and profit,” Smith said, noting that Saile had bootstrapped to $1.6 million annual recurring revenue before securing investors. “Our seed round size reflects us taking only what we need to scale to an outstanding Series A. It’s a responsible growth focus.”

When approached with the unknown, Smith goes back to his baseline: selling. 

“There was all this interest all of a sudden with Saile,” Smith recalled. “Rather than jumping into another raise right away, I ultimately took a step back and decided we need to focus on selling [Saile]bots, building great relationships with customers and building a world-class team.”

In the first quarter of 2023, Saile is set to double its team and invest heavily in engineering and sales. 

“We’re a sales-focused business that scaled to this level with one salesperson — that’s all we had because the technology worked so well,” Smith said. “But now, we are ready to start mass producing Sailebots as much as possible.”

Nick Smith, Saile

Companies are now starting off with more Sailebots that ever, Smith continued, as Saile pivoted its business plan to onboard multiple Sailebots at once.

“Instead of starting with one [Sailebot], we pushed starting with multiple Sailebots to represent the different salespeople on your team,” he said. “We’ve noticed a trend in that direction.”

Saile also has plans to release its first customer-facing management dashboard for Sailebots. A dashboard allows for company executives to measure the performance and productivity of their Sailebots, Smith explained. 

“Our mission is to serve the salespeople and automate the entire prospecting lifecycle, but that doesn’t mean that we have to alienate the enterprise companies they work for,” Smith noted. “We want to make sure that we’re able to serve both from a high level.”

On average, Saile has been growing 7 to 10 percent each month and is targeted to reach $3.5 million annual recurring revenue in 2023, Smith noted.

“I hope we can be even more aggressive than that,” he said, “but that’s a conservative target for now.”

By the fourth quarter of 2023, Smith is set to raise another round of funding, he shared.

“We have a lot of exciting things on the radar for next year,” Smith teased. “… Digital labor is a theme we talk about multiple times a day because really good sales talent is hard to find, and everyone needs more sales — especially in this economic environment. Saile is the solution.”