He picked the single most dreaded phone call in America - customer service - and built an AI that picks it up. Then he taught it to actually solve the problem.
Brian Schiff, mid-laugh in Times Square. The grin of a man whose AI never has to wait on hold.
Brian Schiff runs Flip CX, a New York company whose voice AI answers the calls most people dread making. Order status. A late delivery. A botched return. The robot on the other end no longer reads from a script and dumps you into a queue. It pulls up your order, talks to the backend systems a human agent would touch, and resolves the thing. Across roughly 250 brands, Flip has now handled more than 300 million of these calls, automating up to 90% of inbound volume.
The detail that explains everything: Flip did not start as an AI company. It started as an Uber knockoff. In 2015, Schiff and his co-founder Sam Krut were Cornell undergrads who noticed that ride-sharing services were not yet legal in upstate New York. So they built their own, ran it on campus through Cornell's eLab incubator, and pushed it out to other Upstate college towns.
"Customer service, especially voice support, is expensive, inefficient, and broken."
Running a ride-hailing operation taught them something they had not gone looking for. The hardest part was not the rides. It was the phone - frustrated riders, strained live support, the same broken loop everyone has lived through. In 2017 they made the unglamorous bet: stop selling rides, start fixing the call. The company became a voice assistant, raised a $2M pre-seed in 2019, a $6.5M seed in 2022, and rebranded from RedRoute to Flip CX to signal that it solved a vertical, industry-specific problem rather than a generic one.
That distinction is the whole pitch. Plenty of companies will sell you a chatbot that sounds human. Schiff's argument is that sounding human is the easy 20%. The hard part is the integration - connecting to the order system, the CRM, the warehouse data, the warranty rules - so the AI can finish a real task instead of performing one. Flip built for the messy parts of retail, ecommerce, healthcare and transportation, where a wrong answer has consequences and a phone call is still mission-critical.
In January 2026 the bet paid off in capital. Flip closed a $20M Series A co-led by Next Coast Ventures and Ridge Ventures, with Data Point Capital, ScOp Venture Capital, Bullpen Capital and Forum Ventures along for the round. The raise took a few weeks and drew three term sheets, bringing the company's total funding to roughly $31M.
"We're built for an economic slowdown. While some AI products are propped up on hype, we've earned it by delivering real results for hundreds of customers."
- Brian Schiff, on why Flip isn't a hype tradeNot a horizontal AI that does everything badly. Flip goes deep on retail, ecommerce, healthcare and transportation, where the call is mission-critical and a wrong answer costs you.
The AI connects to order systems, CRMs and warranty rules the way a human agent would - so it completes a real task instead of simulating one.
Pricing tied to usage and outcomes, not seats and hype. Schiff's framing: earn it in deflected calls and happier customers, or don't get paid.
The whole point of his podcast name, Spamming Zero: stop making people mash the zero key to escape. Flip aims to be the help you wanted in the first place.
Volume isn't a vanity metric here - it's the training ground. Every brand and every call sharpens the system that handles the next one.
"Our team is the best thing we've built," Schiff says. A culture-first stance in a category obsessed with model size.
Sources: Flip CX, AlleyWatch. Bars scaled to total raised.
Flip was once a ride-hailing app called RedRoute. The AI pivot came from watching customer support buckle, not from chasing a trend.
They launched ride-hailing in a market the big apps hadn't reached - solving the supply problem before solving the support one.
His podcast is named Spamming Zero - the universal trick of mashing the zero key to escape a phone menu and reach a human.
Before startups, he managed operations for Erik Nates Euro Hockey. The ops instinct showed up early.
Asked about winter plans, he picks indoor tennis courts or the company's LA office over a beach. Focus, even on vacation.
"Our team is the best thing we've built - doubling down on that to achieve our milestones."
- Brian SchiffProfile compiled from public sources. Quotes and figures as reported by Flip CX, AlleyWatch, The Org and Crunchbase.