Today, I’m thrilled to announce Letter AI has raised a $40M Series B, led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we’re seeing in real time: revenue teams aren’t asking for more content or tools. They’re asking for better outcomes, and Letter AI is bringing those outcomes to life.
That’s not the only announcement we are making today. I am also excited to share that we are officially launching Letter Compass, a first-of-its-kind approach to enablement that enriches the content, learning, and insights delivered in Letter AI with deeply personalized context about individual customers & deals.
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We started Letter AI after seeing firsthand the very real enablement needs of revenue teams and the inability for legacy platforms to deliver against them. Even today, incumbent providers are busy consolidating for their own financial gain instead of driving product innovation and outcomes for revenue teams.
Your marketing team can produce great content. Enablement can build phenomenal certifications. Everyone can have intentions. And still, in the moments that matter most, sellers are left to piece it together themselves.
Nobody says, “Let me go check the enablement platform.” They Slack someone. They reuse an old deck. Worst of all: They guess and just wing it.
It’s not because they don’t care. But because the system wasn’t built for how modern revenue teams work.
Deals move fast. Buyers change their minds. Messaging shifts. Competitive context changes overnight. New reps ramp constantly.
Enablement has had the right mission – to help revenue teams win more, win better, and win faster. It just hasn’t had the right operating system.
Letter Compass is the next advancement Letter AI is making to turn that mission into reality.
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