Brian Schiff is the co-founder and chief executive officer of Flip, a voice artificial intelligence company that builds conversational phone systems intended to replace older interactive-voice-response and call-center automation, with a primary focus on retail, e-commerce, and transportation [1][2]. He co-founded the company as an undergraduate at Cornell University with a fellow student he met through a mutual friend, initially building a ride-hailing service for the Cornell campus called Red Route that worked with local taxi operators, modeled loosely on Uber before Uber operated legally in the area [2][3]. As graduation approached and the campus transportation business had no clear path forward, Schiff and his co-founder decided to redirect the company toward voice technology, reasoning that Amazon's Alexa, though imperfect, was already far better than the automated phone systems used by customer service call centers, and they pivoted to building automated call-handling software for taxi and ground-transportation fleets [2][3].
The company subsequently went through several name changes, from Red Route to Flip CX and eventually to simply Flip, a process Schiff described as intentionally deprioritized while the underlying product was being validated, with the eventual one-word name chosen for being easy to search and to represent "dramatic change" [2][3]. In 2022 the company raised 10 million dollars to expand beyond transportation into retail and e-commerce, a vertical Schiff selected because e-commerce companies were more willing than sectors like healthcare or financial services to experiment with new automation technology to improve customer experience [1][2][3].
Schiff has described the rise of large language models as a major stroke of fortune for Flip, arguing that the combination of quality, speed, and cost-effectiveness that LLMs enabled was transformative both for the product itself and for market acceptance of AI-driven phone automation, a concept he says was viewed as "controversial" when the company started roughly five years earlier [2]. He frames Flip's differentiation not around access to underlying AI models, which he considers widely available to all competitors, but around two additional layers: configurable workflows for handling specific call types, such as order cancellations, and integrations with the software systems retailers already use, including order-management platforms like Shopify and Salesforce as well as subscription and returns tools [2]. According to Schiff, the more of these integrations a client enables, the more effective Flip's automation becomes, and he expects the broader AI customer-service category to eventually consolidate around a small number of companies that become synonymous with the market, a position he wants Flip to occupy [2].
Insights & ideas
Brian Schiff frames Flip's core insight as a bet on timing: voice AI only became viable for real customer service automation once large language models reached commercial readiness, and he credits being in "the right moment at the right time" as much as skill for the company's traction [2]. He argues that when Flip started automating support calls five years ago, the idea was considered controversial, and it took the broader AI boom of the last two years to do the market education work of building acceptance for AI phone automation [2]. Schiff also emphasizes vertical focus as a differentiator, breaking the product into three layers, the AI model layer (which he considers commoditized since everyone has access to similar models), the workflow layer, and the integrations layer, arguing that owning specific configurable workflows per industry (like order cancellation logic) is where real competitive advantage lives [2]. He sees the category maturing toward a few dominant household-name players, with room still open to become one of them [2].
Experience
- Co-Founder, CEOFlipJan 2018 to Present
- HostSpamming Zero PodcastJun 2022 to Sep 2023
- Guest LecturerCornell Johnson MBA2018 to 2018
- AdvisorCornell eLab Accelerator, 3 Day Startup2017 to 2018
- Operations ManagerErik Nates Euro HockeyApr 2015 to Jan 2016
Education
Cornell University2014 - 2018
- Mamaroneck High School2010 - 2014
Media & appearances
- Why Work Here: Brian Schiff, FlipWellfound · May 6, 2025
Brian Schiff discusses Flip, a voice AI company that replaces outdated phone automation systems with modern conversational AI, currently focused on retail, e-commerce, and transportation. He explains the founding story starting with an Uber-like campus rideshare app, pivoting to voice automation for taxi fleets, and eventually expanding into retail and e-commerce after raising 10 million dollars in 2022. Schiff also covers how the emergence of large language models has impacted Flip's product development and market positioning.
- From Uber Knockoff to AI SuccessThe OP Show · Sep 3, 2024
Brian Schiff, co-founder and CEO of Flip, discusses the company's evolution from an Uber-like college transportation app called Red Route at Cornell University (2016-2017) to an AI-powered customer service solution. He explains the rebranding journey from Red Route to Flip CX to just Flip, and describes the company's mission to improve AI voice assistants for customer service interactions.
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