Flip Reaches $12M ARR with AI Voice Support for 250 Brands

Flip Reaches $12M ARR with AI Voice Support for 250 Brands

Author: Nathan Latka April 22, 2026 Duration: 24:34

How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls?

Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates customer service calls for transportation, retail, and healthcare brands.

After realizing their Cornell ridesharing app was a dead end, Brian and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation.

You'll learn:

  • How to successfully pivot a failing startup model
  • Why verticalized AI beats horizontal platforms
  • How to implement usage-based pricing at $1.50 per call
  • Why "listen mode" is their best sales tactic
  • How to maintain 75 percent gross margins with AI
  • Why they rejected a theoretical $150 million acquisition offer
  • How to select the right industries for expansion
  • Why competitive B2C markets are best for AI tools

Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year.

Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI 

Connect with Brian:  https://flipcx.com/

Connect with Nathan:  https://founderpath.com/ 


Ever wonder what the actual numbers look like behind a successful software company, or what crucial decision made the difference between stalling and scaling? SaaS Interviews with CEOs, Startups, Founders cuts straight to that chase. Host Nathan Latka sits down each day for a focused fifteen-minute conversation with the people building the software businesses shaping our world. These aren't abstract discussions; you'll hear founders detail their precise revenue figures, customer acquisition costs, team structures, and the sometimes messy realities of growth. The guests on this podcast represent the full spectrum of the journey, from those just launching an MVP to leaders managing companies with thousands of customers, from bootstrapped operators to those navigating venture funding. By tuning in, you get a daily dose of unvarnished data and tactical stories, stripping away the hype to understand how real SaaS businesses are built, run, and monetized. It’s a resource for entrepreneurs, operators, and anyone curious about the mechanics of modern software entrepreneurship, offering a clear window into the strategies that work and the pitfalls to avoid. Latka’s direct approach ensures every interview delivers concrete takeaways, making this podcast a unique and valuable listen for the business-minded.
Author: Language: English Episodes: 50

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