Letter AI has raised $40 million in a Series B round led by Battery Ventures. The Chicago-based company, which builds an AI-native revenue enablement platform for enterprise sales teams, closed the round just four months after its previous raise. Participating investors include Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and a number of existing backers.

The round reflects growing enterprise appetite for AI platforms that go beyond content management and periodic training. As part of the announcement, Battery Ventures Principal Brandon Gleklen has joined the Letter AI board of directors.

Why Revenue Enablement Needed a Rebuild

Revenue enablement has long been one of the more fragmented layers inside large enterprises. Most teams rely on a mix of disconnected tools that never quite work together, leaving sellers with low adoption rates, slow onboarding, and according to Salesforce’s 2024 State of Sales report, less than 30% of their time actually spent with customers.

Letter AI was built from day one as a unified platform with intelligence at its core. Rather than adding AI features on top of older infrastructure, the company designed its system to connect content, learning, coaching, and buyer engagement in one place, adapting in real time to each seller and each active opportunity.

The company positions this as a move from “revenue enablement” to “deal enablement” — bringing relevant guidance directly into live sales situations, not just providing training that arrives after the fact.

A New Product Built Around Active Deals

Alongside the funding, Letter AI is launching Letter Compass, a new product designed to deliver real-time guidance for deals already in progress. By pulling together enablement content, learning materials, live CRM data, and customer interaction history, Letter Compass surfaces highly contextual recommendations at the moment sellers need them most.

The launch signals a clear direction for the company: rather than helping sales teams prepare in advance, Letter AI wants to be present throughout the actual deal cycle.

“AI has made individual enablement features easy to replicate, exposing the limits of point solutions. What enterprises need is a holistic system that understands deal context and supports sellers throughout the lifecycle of a deal.”

Armen Forget, co-founder and CTO of Letter AI

What Customers Are Seeing on the Ground

Lenovo is among the enterprises already using Letter AI to change how enablement fits into its sales process. Abdul Hakim, Executive Director of Digital Workplace Solutions at Lenovo, notes that teams now receive real-time, deal-specific guidance rather than static training that arrives too late, allowing them to respond faster to evolving service offerings and accelerate sales cycles.

Beyond Lenovo, Letter AI works with Adobe, Novo Nordisk, Plaid, Zip, RingCentral, Kong, and SolarWinds, supporting revenue teams across more than 30 countries.

About Letter AI

Letter AI was co-founded in Chicago by Ali Akhtar and Armen Forget, both with backgrounds in AI, product development, and engineering. The platform takes a company’s existing knowledge base and converts it into real-time, deal-specific guidance for go-to-market teams. Rather than organizing static content, it dynamically generates personalized coaching and recommendations based on what is happening in each deal at any given moment.

The company was recently recognized by G2 as the Highest Momentum Leader in Sales Enablement and earned 21 badges in the G2 Winter Reports, reflecting strong customer satisfaction across enterprise and mid-market segments.

Investors Back a Platform Approach to Sales AI

Battery Ventures led this round based on strong customer adoption and rising enterprise demand for AI systems that operate at a platform level rather than as isolated features.

“Letter AI stands out because it wasn’t designed as a content repository or an AI add-on — it was built from the ground up as an AI-native platform that delivers real, measurable impact at the deal level. That’s what modern revenue teams are looking for.”

Brandon Gleklen, Principal at Battery Ventures

Other investors in the round include Y Combinator, Lightbank, Northwestern Mutual Future Ventures, and existing backers. For more information on Letter AI’s investors, visit the respective pages for Battery Ventures, Y Combinator, Lightbank, Northwestern Mutual Future Ventures, and Stage 2 Capital.

Origianl Creator: Ekaterina Pisareva
Original Link: https://justainews.com/companies/funding-news/battery-ventures-leads-40m-round-for-letter-ai/
Originally Posted: Tue, 24 Feb 2026 21:07:07 +0000