Flip raises $20M Series A after automating 300M+ customer service calls with Voice AI

Flip is making a strong case that the phone, not chat, is where enterprise AI gets real. The New York-based startup just closed a $20 million Series A round after its Voice AI platform handled more than 300 million customer service calls for major brands.

The round was co-led by Next Coast Ventures and Ridge Ventures, pushing Flip’s total funding to $31 million. Data Point Capital, ScOp Venture Capital, Bullpen Capital, Forum Ventures, and several angel investors joined in.

At a time when much of the AI spotlight is on chatbots and general-purpose agents, Flip has taken a different approach. It focused on voice from day one and built software meant for real phone conversations, the kind where mistakes cost money and brand trust. Retail, e-commerce, healthcare, and transportation companies use Flip to automate high-stakes calls that still trip up most AI systems.

Voice AI startup Flip lands $20M to scale phone automation for enterprise brands

That bet is paying off. Flip’s tech now answers calls for hundreds of enterprises, including Under Armour, Tory Burch, and Newell Brands. The company says its platform processes around 20 million calls each month, handling everything from order changes to appointment scheduling inside the same backend systems human agents use.

The funding lands at a turning point for enterprise AI. Businesses poured billions into broad AI tools over the last two years, but many are now realizing those systems fall short in real-world operations. Phone support, with its accents, interruptions, emotional customers, and messy workflows, quickly exposes every weakness.

Flip’s approach has been to go deep within each industry rather than trying to serve everyone. It built direct integrations and workflow logic around what actually drives call volume. That vertical focus, the company argues, is why its system outperforms general AI agents.

“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.”

Industry leaders back that claim.

“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.”

Investors see Flip as proof that production-grade AI looks very different from demos.

“As enterprises move from AI experimentation to production, teams like Flip stand out,” said Mike Smerklo, co-founder and managing partner at Next Coast Ventures. “They’ve built a solution grounded in domain expertise, integrations, and real customer outcomes.”

Alex Rosen, managing partner at Ridge Ventures, pointed to scale as the real signal. “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.”

Flip plans to use the new capital to grow its engineering and go-to-market teams across New York, Los Angeles, and the UK. The company is doubling down on retail, healthcare, and transportation, where it already sees strong adoption. Transportation was Flip’s first market, and the company says it now holds more than 60 percent of that market. Retail and e-commerce follow close behind, with healthcare quickly catching up after last year’s launch.

Sam Krut, co-founder and CRO, says building in-house is still tempting for large brands, but reality sets in quickly.

“Building a bespoke solution sounds great, sometimes even required for a large enterprise, but the degree of complexity is extremely high. 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 percent of what we have out of the box today? At Flip, we want customers to get phone AI right the first time.”

Founded in 2018, Flip has spent years refining its voice technology long before large language models went mainstream. That head start shows in production results, not just pitch decks. With hundreds of brands already live and millions of calls flowing through its system every day, Flip is quietly building the case that voice, not chat, may be where enterprise AI proves its worth first.

Flip Team