2023 Startups to Watch: Saile (and its bots) innovates future of sales through digital labor
December 14, 2022 | Channa Steinmetz
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.
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.
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
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.”
Startups to Watch presented in partnership with Social Apex, supported by the Ewing Marion Kauffman Foundation, and independently produced by Startland News.
Social Apex connects you to the modern consumer.
As a digital marketing agency based in Kansas City, Missouri, we create customized marketing experiences to better connect to your customer.
Social Apex works with you hands on with strategic consulting and content geared to drive results and help reach long-term growth.
Kansas City Startups to Watch in 2023
[slide-anything id=”691097″]
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.
For more information, visit www.kauffman.org and connect at www.twitter.com/kauffmanfdn and www.facebook.com/kauffmanfdn

2022 Startups to Watch
stats here
Related Posts on Startland News
Rick Usher: How coffee shop culture fuels KC’s startup ecosystem
Editor’s note: Opinions expressed in this commentary are the author’s alone. Coffee shops play a significant role in the growing success of Kansas City’s startup community. Back in September, Startland News readers offered their top picks for best coffee shops for meetings and I’m taking off on that topic now to dig deeper into the…
LaunchKC grants contest to offer $100K grand prize in 2017
Kansas City’s popular grants competition LaunchKC has raised the stakes for applicants in 2017. Instead of allocating $500,000 via 10 equally-sized grants, LaunchKC will dish out eight awards of $50,000 and one $100,000 grand prize. In 2016, LaunchKC drew more than 400 tech startup applicants for the second year in a row. Applications open on…
Three tips to landing in the Techstars KC accelerator
Techstars new local accelerator is on the lookout for ten tech companies to join the Kansas City accelerator’s inaugural class. In an effort to cull suitable applicants, Techstars KC managing director Lesa Mitchell recently shared some of the top traits the program is looking for in companies. “The Techstars team in Kansas City is…
Photo gallery: Pipeline pitches and the Innovators gala
Pipeline Entrepreneurs celebrated 10 years in style Thursday at the Midland Theater. Check out this photo gallery of the organization’s pitch contest and gala. For more: Here’s a feature story on the gala. Here’s a news story on the award winners. Here’s more background on the organization and its leader, Joni Cobb.




