Announcing Our Series B and Letter Compass Launch

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.

Why We Started Letter AI

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. 

Introducing Letter Compass

Letter Compass directly ties enablement to the individual deals and customers your revenue teams think about day-in and day-out. It unifies your enablement content and training with live deal context from your CRM and what’s actually happening in customer interactions, giving deal-specific guidance to sellers, CSMs, SEs, and others. So instead of “search and hope,” sellers get:

• On-demand, customized coaching tuned to the dynamics of this deal
• Personalized messaging for this customer at this stage in the sales journey
• Curated content for this conversation with these contacts at this account right now
• Personalized sales agent providing deeply tailored insights to win the deal

We believe that enablement isn’t a destination. Enablement is the intelligence layer inside the deal. And that’s what Letter Compass brings to the modern sales organization today.

Learn more about Letter Compass.

The Road Ahead

If enablement doesn’t change the workflow, it doesn’t change the outcome. We’re building Letter AI so the best of what your company knows - messaging, playbooks, product details, competitive intel - shows up when it can actually influence the deal.

That’s the mission, and this new round lets us move faster than ever.

If you’d like to learn more, request a demo today.