Pylon, a three-year-old startup that uses artificial intelligence to automate business-to-business customer service, has raised $31 million in new financing. The round was co-led by Andreessen Horowitz and Bain Capital Ventures and values the San Francisco-based company in the high hundreds of millions of dollars, according to people familiar with the terms. Founded by Chief Executive Officer Marty Kausas, Pylon positions itself as a "Zendesk killer" by routing support requests directly from workplace chat platforms such as Slack and Microsoft Teams. The software layers ticket automation, knowledge management and account intelligence on top of those channels, aiming to replace traditional email-based help-desk tools and reduce response times for post-sales teams. The fresh capital will be used to expand engineering and go-to-market operations as the company seeks to capture a larger share of the crowded AI support market. Pylon’s backers argue that its chat-native design gives it an edge over incumbents adapting legacy systems to newer collaboration environments.