Thirsty Thursday: Chowly CEO Sterling Douglass on Dynamic Pricing, SMB vs Enterprise, and AI for Restaurants

It's another Thirsty Thursday! Paul and Matt interview Sterling Douglass, co-founder and CEO of Chowly, about building the company over a decade from POS integrations into an off-premise platform serving 17,000+ restaurants and the shift from “tablet hell” to today’s dashboard overload. Sterling argues restaurants are embracing the AI wave and that open data access and APIs will beat walled gardens. He explains why Chowly chose to focus on the underserved SMB segment over enterprise, how third-party marketplaces can be partners while Chowly’s dynamic pricing helps operators protect margins, and what operators should look for in acquisitions, emphasizing real product integration and clear customer communication. Sterling also shares stories of SMBs using AI for targeted marketing, discusses Chowly’s platform additions (first-party ordering, loyalty, digital marketing), and previews his new “AI for restaurants” podcast with Aaron Newton of Thanx. This episode is sponsored by OGC - visit: https://onegoalconsulting.com