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

Brian Schiff, co-founder and CEO of Flip (formerly Red Route), details the evolution of his verticalized AI voice assistant from its origins as a Cornell-based ride-sharing app to a leading automation tool for customer service calls. Flip specializes in high-volume consumer sectors including transportation, retail, and healthcare, utilizing deep integrations with industry-specific dispatch and phone systems to automate 85-90% of routine inquiries. The business operates on a usage-based pricing model, typically charging $1.50 per resolved contact, and has achieved an ARR run rate exceeding $12.5 million with 250 active customers. Key growth milestones include a $20 million Series A funding round at a $100 million valuation and the successful expansion into retail with major brands like Under Armour. Schiff emphasizes that vertical specialization provides a competitive moat against horizontal AI platforms by handling complex edge cases out of the box.