Talla Gets $8.3M, Led by Glasswing, to Build Chatbots for Enterprises

In a deal that signals where some artificial intelligence companies are heading, Boston-based Talla said today it has raised an $8.3 million Series A round led by Glasswing Ventures.

PJC (formerly Point Judith Capital) also participated in the round, along with Talla’s previous investors Avalon Ventures, Pillar, and Jason Calacanis’s Launch fund. The new cash brings Talla’s total raised to $12.3 million since its founding in 2015. The company has 17 employees (some pictured above) and says it plans to do some hiring in sales and data science.

The deal is modest compared to, say, Montreal-based Element AI’s $102 million Series A round announced last week (a very different kind of A.I. company). But Talla’s new funding shows that A.I.-based virtual assistants are getting strong interest from investors and, increasingly, from corporate customers.

Rob May

Talla founder and CEO Rob May says he was looking for a more “West Coast-style deal” for his startup’s Series A. “We’re going after market share, trying to build a bigger company. We don’t have non-competes,” he says. “It’s about thinking big and thinking long-term, and trying to do something meaningful.”

Talla has developed a text-based messaging assistant that uses machine learning and natural language processing to automate corporate service desks. Companies can use the conversational “chatbot” interface to answer employees’ human resources questions, IT requests, and so forth. The software runs on platforms like Slack, Microsoft Teams, and the Web. May says customers are using it to answer repetitive questions (think HR benefits), build corporate knowledge bases, onboard new employees, and do “micro-training.”

Outside experts see some promise here. Matt Taylor, the founder of Boston-area A.I. startup Ohmense, says via e-mail that “Talla is a child of Boston and Silicon Valley ideals: simultaneously make your team smarter, faster, and more powerful while inventing a completely new ecosystem for a generation from now.” He adds that the company’s technology is “at the forefront of empowering workers to collaborate with, rather than merely use, machines.” (Taylor, the former chief technology officer of machine learning and fintech company Kensho, is not involved with Talla.)

In a prepared statement, Glasswing Ventures co-founder and managing partner Rudina Seseri calls Talla a “category maker” with the potential to “revolutionize the way employees access information, enhance productivity, and manage tasks.” Glasswing, also based in Boston, is focused on early-stage investments in A.I.-related startups. (As far as I know, Talla is Glasswing’s first investment from its new fund.)

But the challenge, as always, is to get paying customers. Talla says 2,000-plus companies are using or piloting its software, but the vast majority aren’t paying yet.

May thinks that in the public mindset, chatbots are “still bad for the consumer, because of the bad [user] experience. But they’re starting to take off in the enterprise.” Some tech companies working on related problems include Spoke, Troops, and Polly.ai.

So, what will it take for A.I. assistants to gain adoption within big companies? More success stories, May says. “When people realize the productivity [gains], they’ll realize you’re going to be behind if you don’t have a bot strategy,” he says. “You’re going to look around in three years and be shocked at all the things bots can do.”

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