Flip Hits 300M Automated Call Milestone, Raises $20M to Scale Enterprise Vertical AI

• Funding round co-led by Next Coast Ventures and Ridge Ventures; total funding reaches $31M
• Investment underscores Flip’s massive scale: trusted by hundreds of enterprise customers; brands powered by Flip include Under Armour, Tory Burch, and Newell Brands
• Outperforming generalist omnichannel agents, Flip has become the standard for high-stakes voice interactions in retail e-commerce, healthcare, and transportation

NEW YORK--(BUSINESS WIRE)--Flip, the AI solution that automates customer service calls for enterprise brands, today announced a $20 million Series A funding round co-led by Next Coast Ventures and Ridge Ventures. The investment recognizes Flip’s dominance in the customer experience market, where its technology has now handled more than 300 million calls across hundreds of brands.

The round comes as the enterprise AI market reaches a critical inflection point. While billions of dollars have poured into general-purpose horizontal AI agents, enterprises are finding that these broad models often struggle with the complexity required to deliver results in production.

Flip’s Series A marks an ongoing shift toward vertical AI—specialized systems built on deep industry workflows that outperform generalist models. The company will use the capital to accelerate product development and expand its engineering and go-to-market teams in New York, Los Angeles, and the UK to meet surging demand.

Data Point Capital also participated in the round, alongside ScOp Venture Capital, Bullpen Capital, Forum Ventures, and a group of angel investors. This brings Flip’s total funding to $31 million, supporting operations that now extend across North America, the UK, and Australia/New Zealand.

“Customer service is one of the obvious AI opportunities in enterprise, and the vertical approach is emerging as the winning way to do it—maybe not yet in funding, but in traction and customer love. It’s just the only way the technology can deliver on its promise for brands,” said Brian Schiff, co-founder and CEO of Flip. “Rather than huge teams building and integrating custom solutions from scratch, industry-specialized solutions like Flip come with hundreds of integrations and proven workflows for all of the top call drivers that can be easily customized and launched.”

Vertical Intelligence for High-Stakes Customer Experience

With Gartner predicting that 70% of customer service journeys will begin with conversational AI by 2028, the stakes for getting automation right have never been higher. Yet the influx of generalist, horizontal agents has left many brands trapped in costly commitments with subpar results.

Flip’s thesis is that the ultimate winners will not be platforms chasing every use case, but specialized systems that are easy to manage and deliver huge business outcomes. While competitors rely on surface-level chat interfaces, Flip has spent years building the deep technology integrations required to solve the industry’s most challenging problem: automating the customer service phone call.

Proven Results for Industry Leaders

Choosing an AI to speak directly to customers is a high-stakes decision. As a result, major brands are increasingly relying on peer validation from those who have already successfully made the leap to identify the right partner. For Flip, this focus on proven outcomes has driven a surge of inbound demand from leaders across the retail, healthcare, and transportation sectors.

“AI was a strategic goal to amplify the Tory Burch brand in 2025,” said Stuart Benzal, VP Client Services at Tory Burch. “With Flip, we went from vision to reality, fast. After trying and failing with other vendors, Flip delivered with real business impact—and it was obvious they would from our first meeting.”

“Flip was a launch partner for our ecosystem, and has seen tremendous adoption,” said Kevin Clarke, SVP Strategic Business Development at Experity. “The product delivers, the team is great, and customers truly love them.”

“When we looked at taking our customers’ voice channel to the next level, Flip was head and shoulders above the market,” said Philip Macartney, Chief Commercial Officer at iCabbi, a subsidiary of Groupe Renault. “Not only do they have a robust and reliable AI product, but they also keenly know and understand our clients’ challenges. We felt this combination would not be beaten, so we have gone all-in with a strategic white-label solution that, even at this early stage, is driving real, demonstrable results for our clients. iCabbi is excited about where this unique relationship can go next.”

Investor Perspectives on $20M Series A Round

“As enterprises move from AI experimentation to production, teams like Flip stand out,” said Mike Smerklo, Co-Founder and Managing Partner of Next Coast Ventures. “They’ve built a solution grounded in domain expertise, integrations, and real customer outcomes.”

“While the market is still experimenting with AI concepts, Flip is already operating at an industrial scale. Processing 20 million calls a month for 250 global brands proves that deep vertical integration is the only way to solve complex service workflows,” said Alex Rosen, Managing Partner at Ridge Ventures. “We invested because Flip is the clear category leader delivering measurable value today.”

Expanding in High-Demand Verticals

Flip plans to scale its engineering and go-to-market organizations, dedicating specialized product teams to each of its core verticals as it deepens integrations in retail, healthcare, and transportation. Flip’s AI assistant answers calls instantly, integrates with the same systems human agents use, and autonomously completes the top workflows that drive the majority of call volume.

The company has already secured over 60% market adoption in the transportation vertical, its first market. In retail and e-commerce, Flip has established itself as the early category leader, while its launch into healthcare last year has fueled exponential growth.

“Building a bespoke solution sounds great, sometimes even required for a large enterprise, but the degree of complexity is extremely high,” said Sam Krut, co-founder and CRO at Flip. “Even with something simple like canceling an order, there are multiple integrations and dozens of edge cases. Why would any brand want to spend the next five years building itself 10% of what we have out of the box today? At Flip, we want customers to get phone AI right the first time.”

About Flip

Flip is the leading phone AI provider for retail e-commerce, healthcare, and transportation. Leveraging years of proprietary voice AI development, Flip provides an integrated AI assistant that answers calls instantly and autonomously resolves complex customer issues end-to-end. Founded in 2018 and headquartered in New York City, the company has raised $31 million to date. For more information, visit flipcx.com.