Sailes closes $5.1M investment round led by STL firm, with KCRise Fund, Wichita VC

The foundation for Sailes has always been solving difficult problems for sales teams, said Nick Smith; the success of a Series A funding round for the startup will power new tools toward that goal. 

“Everyone is on this AI hype train, and we’ve been for AI for a while. But it’s not just about using as much AI as possible,” said Smith, who co-founded Sailes alongside Clive Cadogan in 2018. “It’s about solving hard sales problems. People waste a lot of time on random outreach and following up with leads. The products we’re releasing help them with that.” 

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Sailes is a SaaS AI solution that automates the prospecting life cycle through Sailebots that perform Digital Labor (which measures how many human-worthy prospecting tasks the Sailebot performs on behalf of the human) sales tasks for mid-market and global enterprise businesses.

Click here to check out Sailes. 

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Sailes announced Thursday it closed a $5.1M Series A round, led by Lewis & Clark Ventures in St. Louis. Other investors include KCRise Fund, Wichita-based Tenzing Capital,  Acronym Venture Capital, and Valor Ventures.

The round brings the company’s total funding to $6.6 million.

“From the early stages of our diligence process, it became apparent that Sailes was the first mover in using AI to fully automate the lead generation and prospecting activities for enterprise sales teams,” said Michael Rockhold who serves as principal at Lewis & Clark Ventures and a board member for Sailes. “… As evidenced by their tremendous growth and marquee customer logos, Sailes is experiencing a strong pull from the market. Additionally, Nick and team embody all of the characteristics we look for when backing early-stage founders.”

Click here to read why Sailes was selected as one of Startland News’ Kansas City Startups to Watch in 2023.

The $5.1 million funding is expected to be used to build a machine learning specific team, Smith noted.

“We have a lot of great talent on the engineering side; but our Sailebots have uncovered so much data over the past four to five years, that we really needed a machine learning team to take that data and productize it so that users have value for it,” Smith explained. “The first release from them will be Predictability. … With Predictability, we’ll be able to tell the user their likelihood of success, meaning who wants to talk to them, before they do any outreach at all.”

Predictability will be part of Sailebot Model 2, which is set to come out late September/early October, Smith continued. Sailebot Model 2 is an even more robust AI model that still reads and reacts to emails, but it also applies machine learning to the contacts that it is sourcing and to the ability to overcome objections.

Nick Smith, center, and members of the Sailes team at Startland News’ 2023 Startup Crawl in June; photo by Tommy Felts, Startland News

This summer, Sailes launched Starboard — a platform that allows users the direct ability to edit and train their Sailebot or fleet of Sailebots.

“We released our dashboard earlier this year, and that now lives in the Starboard,” Smith said. “Now in addition to the visibility, they have the ability to control their bot and change it and see the data it’s generating. They can train it to overcome objections. So say someone is a paper salesman, and they get a response that the potential customer only buys from Dunder Mifflin. The Salesbot will generate a response to overcome that objection. The salesperson can then edit and train their bot, so it always knows how to respond to that objection.”

KCRise Fund portfolio companies honored as Startland News’ Kansas City Startups to Watch in 2023: Liam Reilly, KCRise Fund; Nick Smith, Saile, Emily Brown, Free From Market, Darcy Howe, KCRise Fund; Charles Clow, Whipz; Ryan Wasinger and Randy Wasinger, CryptoSlam; photo by Tommy Felts, Startland News RELATED: KCRise Fund closes $34M Fund III with ‘hyper-local’ focus; Here are its first four investments

Prior to Starboard, customers would have to meet with Sailes’ success team in order to train and work with their Sailebot. Now, the process is streamlined to incredible ease and efficiency, Smith said.

“Our success team is involved with ramping up the usage of Starboard and working with the customers so that they know how to use it,” he said. “One of the things we learned is that they love working with our team and don’t want to lose that — and they won’t. We’re not taking our team away. We’re just giving our customers more control.”

The Sailes team will continue to grow, with openings in engineering, operations, sales and marketing, Smith added.

Sailes (formerly known as Saile) recently rebranded, Smith said, noting that he had originally wanted to name the Sailes.

“There’s actually a Metallica story there,” Smith explained, smiling. “Metallica won the MTV Icon award, and when the actor Sean Penn gave them the award, he said, ‘When I heard their [band] name, I thought it was way too on the nose. They’ll never make it.’ I always wanted to call the company Sailes, but I thought it was too audacious. But Sailes is sales with AI! So we went for it.”