2023 Startups to Watch: Saile (and its bots) innovates future of sales through digital labor

Editor’s note: Startland News selected 10 Kansas City scaling businesses to spotlight for its annual Startups to Watch list. Now in its eighth year, this feature recognizes founders and startups that editors believe will make some of the biggest news in the coming 12 months. The following is one of 2023’s companies.

Click here to view the full list of Startups to Watch — presented in partnership with Social Apex, supported by the Ewing Marion Kauffman Foundation, and independently produced by Startland News.

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When Nick Smith launched Saile nearly five years ago, he envisioned salespeople working alongside their Sailebots to accomplish everyday tasks, he shared. Now, companies are embracing and highlighting the role of Saile’s technology — with several including Sailebots in their official org charts.

“Multiple customers, who have never spoken to each other, came to us to show us what a Sailebot would look like in their organizational structure. It was a mind blowing experience to see it laid out, and it is future evidence of the importance of the dashboard we’re building out for manageability,” said Smith, who co-founded Saile.ai with Clive Cadogan in 2018. 

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Elevator pitch: Saile triples the prospecting power of the world’s best sales reps with its patent-pending, personality-driven Sailebots. Beyond marketing automation, Sailebots are AI that automate the entire prospecting lifecycle: research and discovery, engaging and following-up with stakeholders, making intelligent decisions and delivering revenue opportunities to humans and their customer relationship management. 

• Founders: Nick Smith, Clive Cadogan
• Founding year: 2018
• Current employee count: 18
• Amount raised to date: $1.55 million
• Noteworthy investors: KCRiseFund, Valor Ventures

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Saile.ai 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.

Catching the interest of regional and national investors, Saile closed a $1.35 million seed round in November. A portion of the funds will be used to build a customer-facing management dashboard, which is set to launch in the upcoming weeks, Smith teased.

“For so long, the only deliverable a Sailebot has sent its owner is an actionable lead,” Smith said. “Because that’s the only deliverable, there tends to be a lot of focus there — but a Sailebot does so much more. It’s finding contacts; it’s following up on referrals; it’s reaching out to them at the time they request, etc. The dashboard allows us to demonstrate that visual element, so that [the customer] knows all the work that is being done.”

Click here to read more about Saile’s recent $1.35M funding round.

Saile’s dashboard also allows for companies to see how their Sailebots rank against one another, allowing for future optimization of Sailebots, Smith explained. 

“We’re trying to add some action to Digital Labor and show where a Sailebot is spending its time — not just how much time it’s spending,” he noted. “Because if a Sailebot in a company is having more success than another one, or it’s taking less tasks to generate a revenue opportunity, there’s an action there. There’s an optimization there. It’s an insight, something we can learn.”

Continuing to enhance Sailebots will be important as the future of the sales industry becomes more saturated, Smith added. 

“Right now, there’s an abundance of tools, of logins and dashboards — and I think that will eventually saturate sales,” Smith explained. “People will need help because it’s weighing everyone down. The only people who are really making it are those salespeople who have their eye on the ball of closing business, creating solutions and talking to customers. There will be a need to multiply those people. 

“We’re coming out of, I believe, the mass enablement phase,” he continued. “Say [a company] has a top salesperson, and they wish they had three more of them; but they also have eight other people. They could enable all of them with the right tools to become as good as the top person.” 

The tool Smith is referring to: Sailebots — personalized sales robots that would allow for companies to multiply their workforce through Digital Labor. 

“It sounds like a self-serving answer, but it’s what we’ve thought for a while,” Smith said. “There’s a diminishing return by adding sales tool after sales tool to your toolbox. But I do think the idea of multiplying the best salespeople is a trend we will see.”

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Startups to Watch presented in partnership with Social Apex, supported by the Ewing Marion Kauffman Foundation, and independently produced by Startland News.

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Kansas City Startups to Watch in 2023

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Startups to Watch is possible thanks to support from the Ewing Marion Kauffman Foundation, a private, nonpartisan foundation that works together with communities in education and entrepreneurship to create uncommon solutions and empower people to shape their futures and be successful.

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