How many times have you and your co-workers asked the same questions on Slack? I know for my team at BostInno and its parent company, American Inno, the answer is quite a lot.

Now imagine a company with over 200 employees trying to field all of those repetitive questions every day — questions about the Wi-Fi password, how to set up a new employee and the company’s policy on maternity leave. That’s a lot of wasted time if someone is actually taking time out of their day to answer every single question.

Rob May.
Rob May.

So why not automate that process using artificial intelligence? That’s the basic pitch behind Talla, the Boston startup started by Backupify founder Rob May that brings AI-powered service desk software right inside Slack or Microsoft Teams.

After convincing over 2,000 companies to use the service — and a few dozen of them to become paying customers — the startup has raised an $8.3 million Series A round led by Boston-based venture capital firm Glasswing Ventures to make a bigger sales and marketing push, as well as invest further into Talla’s natural language processing infrastructure. The round, which brings total funding to roughly $12.3 million, also included PJC, Pillar, Avalon and Launch as investors.

Using machine learning and natural language processing, Talla’s software is able to build a knowledge graph of a company’s processes — specifically in IT and human resources — by learning from the answers that users provide to questions posted in Slack. The software also lets administrators send out service alerts or news updates, start employee training or collect poll results. In the future, there are plans to use large data sets collected by Talla to provide advanced functionality.

May, Talla’s CEO, told BostInno that there are already a number of players in the service desk software space, including ServiceNow and Jira. But what those existing systems have been lacking is automation, which is why May believes Talla is well-positioned to lead the next wave of service desk companies.

“Most of the time when you want to increase your internal level of service, you’re going to drive up to your costs,” May said. “With AI technologies, you can drive down your costs and provide a better level of service.”

“With AI technologies, you can drive down your costs and provide a better level of service.”

Beyond those two benefits, May said Talla has helped increase the level of employee engagement at companies, compared to when companies would only send out information over email. One company, for example, has used Talla to send employees direct notifications on Slack about their open enrollment deadlines for health insurance and has found a higher response.

Talla’s paid customers “are in the dozens,” May said, out of the more than 2,000 companies that are using the service — highlighting the challenge AI software companies face with adoption. May said while it’s easy to “fill the top of the funnel,” most companies haven’t developed new processes for evaluating AI systems. Since AI systems only become more valuable as they accumulate more knowledge over time, it can be difficult for companies to see their long-term value at first.

“We’ve refocused our sales process around helping people understand that,” he said.

While Talla’s first two monthly pricing tiers are $59 and $499, May said he is currently working on some enterprise deals that are in the four figures per month. He said one Fortune 50 company with 90,000 employees is currently doing a pilot — which could bring in significant revenue even if a fraction of those employees use the system. Talla’s enterprise pricing charges $5 per user every month, meaning it could potentially pull in six figures in annual revenue from one company alone.

Talla is one of the first investments made by Glasswing, one of the local VC firms that is riding the growing wave of investments in AI startups, as highlighted in BostInno’s AI in Boston series earlier this year.  The firm was launched last year by Rudina Seseri and Rick Grinnell, who were former partners at Fairhaven Capital Partners in Cambridge for nine years. Seseri told me that Glasswing will have more funding announcements to share in the near future.

“We think AI will be a pervasive layer of the enterprise,” she said.

Talla, one of BostInno’s 17 startups to watch in 2017, has around 17 employees and plans to hire in sales and data science.