Cash plus connections: how Flip scaled with debt to a $20M Series A

In a market flooded with generic, do-everything AI, Flip has spent years proving a contrarian bet: going deep in a few industries beats going wide across all of them. The New York-based company builds the "Alexa for customer service" — a voice assistant that answers high-volume customer calls, instantly resolves the routine ones, and seamlessly hands the complex ones to human agents.

Its origins are surprising. Co-founders Brian Schiff, Sam Krut, and Jacob Cooper first built a ride-hailing app called Red Route as undergrads at Cornell, back when Uber was banned in upstate New York. The experience surfaced a bigger opportunity in customer service, and by 2018 the team had fully pivoted into what is now Flip — starting with transportation companies before expanding into retail and, later, healthcare.

RBF fuels growth — and a well-timed intro

Long before making headlines, Flip faced the challenge every early-stage founder knows: it needed capital to build, but not at the cost of equity or control at such a formative stage.

In two short years, the company deployed $1.1 million in revenue-based financing from Lighter Capital, across three rounds, to invest in product, expand across industries, and make key hires — without giving up ownership or equity. Just as importantly, it freed Schiff to focus on the product instead of pitch decks and investor meetings. The results followed: a 3x increase in customers and a 10x increase in revenue.

When Schiff was ready to raise his next round, Lighter did something a lender rarely does — it opened its network. 

Lighter guided Flip through the process and made introductions that helped land a $6.5M seed round led by ScOp Venture Capital and Bullpen Capital, with a group of angel investors.

Going deep, not wide

That seed capital fueled the bet that now defines Flip: a vertical approach. Rather than building a horizontal, industry-agnostic platform that has to be custom-built and integrated for every new customer, Flip comes ready out-of-the-box for the specific industries it serves — moving from transportation into retail in 2021 and healthcare in 2024.

The company is just as disciplined about economics. It charges per automated call, with no upfront cost or long-term commitment, and it runs lean — capital efficiency its investors have praised. In a space Schiff describes as full of noise from generic AI providers chasing every industry at once, Flip's depth has translated into real, at-scale deployments and marquee customers including Under Armour, Tory Burch, and Newell Brands.

The payoff: a $20M Series A

In January 2026, that traction culminated in a $20M Series A, co-led by Next Coast Ventures and Ridge Ventures, with Data Point Capital joining returning backers ScOp Venture Capital, Bullpen Capital, Forum Ventures, and a group of angels. 

The round brought Flip's total funding to $31M, at a valuation the company says has tripled since its seed round. Flip has reached eight-figure ARR, growing 3x year over year, and its AI has now handled more than 300 million customer calls.

Investors point to the vertical strategy and capital discipline as the differentiator. As one of Flip's new lead investors put it, "a vertical approach yields the best results" — and Flip has quietly launched more live, at-scale deployments than much larger, better-funded rivals, several of which lean on heavy engineering just to make their product work.

It's a trajectory that traces straight back to a scrappier moment — when the right non-dilutive capital, and the right introduction, helped a focused team keep building on its own terms. Cash plus connections, indeed.