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Exclusive: Flip Raises $20M Series A For Its Verticalized Approach To AI-Based Customer Service

Illustration of conversation bubbles. [Dom Guzman]

, a startup that claims to offer an Alexa-like voice AI experience for businesses, has raised $20 million in a Series A funding round, it tells 禁漫天堂 News exclusively.

CEO and CRO met a decade ago in college and began building different ventures together. After a few pivots, they raised funding for New York-based Flip in 2018 with the goal of building AI that 鈥渁nswers and automatically resolves routine requests鈥 for customers calling into a variety of businesses. They started with a focus on transportation companies and moved into retail in 2021 and healthcare in 2024.

AI-based customer service is a saturated space, but Schiff claims Flip鈥檚 approach is differentiated because it鈥檚 a vertical one that is very focused on just three industries.

Brian Schiff and Sam Krut, co-founders of Flip. [Courtesy photo]
Brian Schiff and Sam Krut, co-founders of Flip. [Courtesy photo]
鈥淲hile horizontal industry-agnostic 鈥榩latforms鈥 require custom-building the experience and integration, vertical players like Flip come ready 鈥榦ut-of-the-box鈥 with everything brands in that industry need built in,鈥 Schiff told 禁漫天堂 News.

Among vertical players, Schiff claims that Flip has an advantage because its AI 鈥渋s battle-tested on more than 300 million phone calls.鈥

and co-led the round for Flip, which says it has raised a total of $31 million in funding. also participated in the round, alongside , , and a group of angel investors. Flip declined to reveal valuation, saying only that it was up 3x compared to its seed raise.

Year-over-year growth

Today, Flip has hundreds of enterprise customers, including , , and global transportation companies. The company has reached an eight-figure ARR, growing 3x year over year, according to Schiff.

Interestingly, the idea for Flip came when Schiff and Krut were students at . They had built a ride-hailing app called Red Route for calling taxis at Cornell, at a time when was still banned in upstate New York. It was during that experience they came up with the idea for what is today Flip.

鈥淐ustomer service is one of the obvious AI categories for business, and we’re talking on a daily and weekly basis with the largest brands on the planet,鈥 Schiff said. 鈥淓ven for them, it’s not a question of 鈥榠f.鈥 It’s a question of 鈥榳hen鈥 and 鈥榳ith whom.鈥欌

That, he said, has created 鈥渁 huge amount of noise鈥 in the market.

Over the past year or so, a number of what Schiff described as 鈥済eneric AI providers鈥 popped up.

鈥淭he great irony of this space right now is that while all of the headlines and much of the funding has gone into these generic platforms that are trying to be the AI everything for everyone, across every industry, every channel, every use case. In reality, most of the actual traction, most of the successful customer stories, are working with vendors like Flip that are going very deep into one or a couple of specific industries,鈥 Schiff told 禁漫天堂 News in an interview.

Another differentiator, in his view, is that few companies have developed deep expertise with AI telephone customer service.

鈥淢ost people are doing it inside of chatbots or auto email responders,鈥 he said. 鈥淲e really look at the quality of the experience. It doesn’t matter how nice it is to talk to 鈥 it’s still just another bot that’s in the way of a customer trying to solve their problem.鈥

When it comes to the revenue model, Flip doesn鈥檛 charge an upfront cost or require a long-term commitment. Rather, it charges per automated call 鈥 a usage model it has implemented since its early days.

鈥楢 vertical approach yields the best results鈥

, managing partner at , believes that customer service is one of the few huge markets where generative AI has produced tangible results for enterprise customers and a better experience for users.

鈥淏ased on our 30+ years of investing in software, we believe a vertical approach yields the best results,鈥 he wrote via email. 鈥淔lip has taken a different approach than many others by focusing on a couple of verticals and going really deep 鈥 While there are plenty of competitors making noise, some are going after different parts of the market, and Flip has quietly, up to now, launched more live customer deployments, at scale, than anyone.”

, co-founder and managing director at , said he has spent nearly two decades in and around call centers and voice technologies and has 鈥渘ever seen a more compelling ROI for customers鈥 than what Flip offers.

He added: 鈥淭he founding team is exceptional, customer feedback has been tremendous, and the potential for Flip to become a $1 billion business is clear.鈥

Smerklo said he is also impressed with the company鈥檚 capital-efficient approach to growth.

鈥淪everal other companies that have raised tremendously more money have to rely on ‘forward engineering’ to get their product to work for customers,鈥 he said. 鈥淔lip’s solution works, doesn’t require a massive investment from customers, and solves real, salient business issues.鈥

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