Letter AI just pulled in 40 million in Series B funding . This is a huge step for this Chicago startup as it ramps up its AI revenue tools for go-to-market teams. Battery Ventures led the round along with Y Combinator, Lightbank, Northwestern Mutual Future Ventures, and Stage 2 Capital.
What's wild is that this comes only four months after their Series A closed at the end of 2025. That kind of speed says a lot about how much investors believe in what Letter AI is building and how fast big sales teams are jumping on board. With this round, their total funding now sits somewhere in the "hundreds of millions, at least according to the latest reports.
Funding for an AI-First Enablement VisionLetter AI is a company that specializes in revenue enablement technology and is fully focused on developing generative AI. Letter AI was founded in 2023 by Ali Akhtar and Armen Forget. It is a new company aiming to redefine revenue enablement by providing real-time intelligent assistance directly in the seller's workflow.
