Flip, a New York–based voice AI startup, has raised a $20 million Series A to try to fix one of the worst parts of the customer experience: calling support, battling through a phone tree, and shouting “representative” into the void.
Flip’s new round and who’s backing it
The Series A was co-led by Next Coast Ventures and Ridge Ventures, with Data Point Capital, ScOp Venture Capital, Bullpen Capital, Forum Ventures, and several angel investors also participating. The new funding brings Flip’s total capital raised to $31 million and gives the company extra runway as large brands lean harder into AI-driven customer support.
Flip sits in a crowded space, but its pitch is straightforward: replace legacy IVR systems with a phone-first, Alexa-like voice assistant that can actually handle the call instead of just routing it.
From Cornell taxis to handling 300 million calls
Co-founders Brian Schiff and Sam Krut met at Cornell about a decade ago. Their first startup, Red Route, was far from a pure AI play. It was a practical fix for a campus problem: making it easier to hail Cornell taxis at a time when Uber still faced restrictions upstate.
Red Route built a dispatch app for taxi operators. The real lesson, though, came from what was happening off-screen. Dispatchers and riders were constantly stuck in phone queues, fighting with clunky phone systems that looked and sounded like they hadn’t been updated in decades.
“Most AI demos look great in a browser,” said co-founder and CEO Brian Schiff. “But the real-world problem is the phone call. That’s still where the pain lives.”
That insight pushed the founders to rethink the phone call itself as the product.
“If every ride started and ended with a bad phone call, maybe the phone call was the real product,” Schiff recalled.
In 2018, they pivoted from Red Route into Flip, betting that voice AI could do for customer service calls what Amazon Alexa did for the smart home: make it feel natural to speak to software.
Today, Flip’s platform answers and resolves routine support calls for more than 250 brands worldwide. The company says it now processes around 20 million calls per month and has handled over 300 million calls in total across retail, e-commerce, healthcare, and transportation. Customers include Under Armour, Tory Burch, and Newell Brands.
Why investors think phone-first AI’s moment has arrived
For Next Coast Ventures, the bet on Flip is part technology story, part timing story. Managing partner Mike Smerklo has spent much of the past two decades looking at call center software and voice technologies. Flip, he argues, is one of the first to make the numbers really work at scale.
“I’ve never seen a more compelling ROI for customers than what Flip is delivering,” Smerklo said. “Voice has been ‘the next big thing’ for 20 years. These founders are finally making it real in production.”
Ridge Ventures partner Alex Rosen points to usage, not hype, as the proof that something has clicked. Flip isn’t sitting in endless pilots or dev sandboxes; it is answering live calls from impatient, stressed-out customers who care about getting help, not about whether the “agent” is human.
“Processing 20 million calls a month for 250 brands is the signal,” Rosen said. “It proves that deep vertical integration is the only way to solve complex service workflows at scale.”
Big cloud providers like AWS, Google, and Microsoft already sell the building blocks for voice bots. Flip has deliberately chosen a different lane. Instead of a box of parts, it sells a finished product: a phone-first system with industry-specific workflows, prebuilt integrations, and behavior tuned for support calls.
For enterprises, that means Flip isn’t asking them to stitch together their own contact center AI stack. The pitch is to swap out the IVR for something that sounds more natural, taps into the same backend systems as human agents, and starts deflecting calls from day one.
A vertical AI play in a noisy support market
Customer support has become one of the most competitive corners of applied AI. Horizontal platforms—cloud contact center suites, generic chatbots, omnichannel automation tools—promise to cover every channel at once: email, chat, social, and phone.
The problem is that real-world customer conversations get messy. They are emotional, full of jargon, and heavily shaped by industry rules and legacy systems. That is where broad, one-size-fits-all approaches tend to struggle.
Flip is betting on a narrower approach. It is building what the founders describe as “vertical AI” for phone calls, currently anchored in three sectors: transportation, retail and e-commerce, and healthcare. Transportation was the first big wedge, where Flip says it now holds more than 60% market share in certain segments. Retail followed, and then healthcare, which began to ramp in 2024 as compliance and integration hurdles caught up with demand.
Schiff argues that Flip’s advantage comes from going deep in a handful of industries rather than trying to sit above all of them.
Under the hood, that means the AI isn’t just listening for keywords. It’s been trained around common call reasons, the exact steps required in backend systems, and the regulatory and compliance obligations that shape what agents can and cannot say.
The longer the company runs, the more call data it accumulates. With more than 300 million calls processed, Flip has built up a proprietary dataset of call patterns, edge cases, and failure modes that upstarts and generic platforms don’t yet have.
None of that makes the business bulletproof. Hyperscalers could decide to harden their own voice AI offerings and bundle them deeply into cloud contact center products. Established vendors like NICE and Genesys could acquire younger voice AI startups and lean on their existing distribution. Horizontal platforms could spin up their own “vertical” modules for transportation, retail, or healthcare and nibble away at Flip’s lead.
Schiff is blunt that the core AI ingredients are getting easier to access.
“AI infrastructure is becoming a commodity,” he said. “The moat won’t be the model. It will be the workflows, the integrations, and the trust we build by actually picking up the phone.”
A business model tied directly to call deflection
Unlike traditional SaaS tools that charge per seat with annual commitments, Flip charges per call. There is no upfront platform fee and no long-term contract requirement.
That pricing model is designed to align incentives. If Flip deflects more calls away from human agents, the customer pays more—but only because they are saving even more in labor and improving response times. If the system underperforms and call deflection drops, so does Flip’s revenue.
Investors read that as a sign the company is confident in its product. Flip says it has reached eight-figure annual recurring revenue and is growing roughly 3x year over year, though it has not disclosed specific revenue figures or valuation for this round.
The per-call approach also lowers the barrier to getting started. A head of customer experience doesn’t have to rip and replace their entire contact center stack. Flip can plug into the existing setup, start with a narrow slice of call types, and prove out ROI in a matter of weeks before expanding.
That “land and expand” motion has become the backbone of Flip’s go-to-market strategy. The company now leans on direct enterprise sales into large brands across its three target verticals, with integrations into the CRM and contact center platforms those companies already run. In healthcare, where the stakes and regulations are higher, Flip is also working with ecosystem partners and launch collaborations to get in the door.
New funding, bigger ambitions
With $20 million in fresh capital, Flip is planning a hiring push across engineering, sales, marketing, and customer success. The company is also building out hubs in New York, Los Angeles, and the UK to support a broader international footprint and go deeper with existing accounts.
The next 18 to 24 months will be a stress test. Internally, Flip will be under pressure to hit aggressive ARR milestones, grow its footprint in healthcare, and prove that voice AI can reliably handle the bulk of routine calls without hurting customer satisfaction or brand trust.
Externally, it is racing against two fronts: fast-moving startups trying to carve out their own niches in support automation, and trillion-dollar cloud providers that increasingly see customer service as one of AI’s clearest revenue engines.
Schiff keeps the mission statement simple.
“If we do our job, no one will ever have to ‘press 1 for billing’ again,” he said. “They’ll just say what they need, get it done, and hang up. And they won’t care if it was an AI that picked up.”
Fix the phone call first
In a market saturated with chatbot screenshots and generic copilots, Flip is making a narrower promise: fix the phone call before anything else. If it can pull that off, the company could do more than squeeze a bit more life out of voice in an AI era.
The bet is that voice can become the most human-feeling channel in customer service—even when there isn’t a human on the other end of the line.
