Letter AI Raises $40M Series B to Bring Deal-Level Intelligence to Revenue Enablement

Led by Battery Ventures, the round comes just four months after the company's previous raise, as enterprise revenue teams turn to AI to improve deal outcomes

CHICAGO, Feb. 24, 2026 /PRNewswire/ -- Letter AI, the AI-native revenue enablement platform for the world's leading go-to-market teams, today announced it has raised a $40 million Series B funding round led by Battery Ventures, with participation from Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and existing investors. The new funding will be used to scale product development, expand the team globally, and accelerate go-to-market efforts as enterprises move away from fragmented, low-adoption enablement tools toward AI-native platforms built for modern revenue teams.

Letter AI helps companies like Lenovo move beyond traditional revenue enablement towards deal enablement – bringing intelligence directly into live opportunities where it can have the greatest impact on sales outcomes. "Letter AI has changed how enablement shows up in our sales process," said Abdul Hakim, Executive Director, Digital Workplace Solutions, Lenovo. "Rather than relying on static training that arrives too late, our teams now get real-time, deal-specific guidance that adapts to individual seller strengths and the realities of each opportunity. That level of personalized, in-the-moment intelligence has allowed us to respond much more quickly to evolving service offerings and accelerate sales cycles in ways we simply couldn't before."

Letter AI is Rebuilding Revenue Enablement for the AI Era

Revenue enablement has become one of the most fragmented layers in the enterprise stack, with companies relying on disconnected tools that lead to low adoption, slow onboarding, and sellers spending less than 30% of their time with customers (source: Salesforce State of Sales, 2024). Unlike legacy platforms that retrofit AI onto static architectures, Letter AI was built from day one as a unified platform with intelligence at its core – connecting content, learning, coaching, and buyer engagement into a single system that adapts in real time to each seller and each deal.

Real-Time Deal Intelligence for Go-to-Market Teams

Alongside the funding, Letter AI is launching Letter Compass, a new product that delivers real-time, deal-specific guidance for active opportunities. By combining enablement content and learning with live CRM data and customer interactions, Letter Compass brings highly contextual intelligence directly into the flow of sales execution.

"Revenue enablement is a perfect problem for an AI-native platform because it sits at the intersection of content, people, and live decision-making," said Ali Akhtar, co-founder and CEO of Letter AI. "Legacy tools were built for static libraries and periodic training. We built Letter AI for modern sales teams who need guidance that is personalized, contextual, and available in the moment a deal is happening."

"AI has made individual enablement features easy to replicate, exposing the limits of point solutions," said Armen Forget, co-founder and CTO of Letter AI. "What enterprises need is a holistic system that understands deal context and supports sellers throughout the lifecycle of a deal."

Battery Ventures led the round based on strong customer adoption and growing enterprise demand for system-level AI platforms in revenue operations. "Revenue enablement is undergoing a fundamental reset," said Brandon Gleklen, Principal at Battery Ventures, who has joined the board of Letter AI. "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."

"Sales methodology has historically lived in static playbooks that reps skim once and forget. Letter AI changes that – it's a living intelligence layer that's tuned to every call prep, embedded in every live interaction, and actively shaping next steps for each deal," said Mark Roberge, co-founder at Stage 2 Capital and founding CRO of HubSpot. "What makes this truly transformative is the personalization – the guidance is customized to each buyer's unique context, and the coaching adapts to where each seller is in their own development journey. Letter AI meets sellers where they are – always on, always relevant, and always adapting to the changing buyer landscape."

Note to editors:

Letter AI 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 adoption, satisfaction, and growth across enterprise and mid-market segments.

The Media Kit with video, executive biographies and photos / imagery is available here.

About Letter AI

Letter AI is an AI-native revenue enablement platform that turns a company's existing knowledge into real-time, deal-specific guidance for go-to-market teams. Rather than organizing static content and training, Letter AI dynamically generates personalized enablement and coaching based on live deal context, so sellers get what they need in the moment a deal is happening. Built from the ground up as a platform, Letter AI connects content, coaching, learning, and buyer engagement into a single intelligent system, driving higher adoption, faster onboarding, and more time spent with customers.

Letter AI is trusted by global enterprises, including Lenovo, Adobe, Novo Nordisk, Plaid, Zip, RingCentral, Kong, and SolarWinds, and supports revenue teams across more than 30 countries. Headquartered in Chicago, the company was co-founded by seasoned AI, product, and engineering leaders, Ali Akhtar and Armen Forget, and is backed by Battery Ventures, Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and other leading investors. For more information, visit www.letter.ai.

Media contact:
Nick Morris | [email protected] | +44 (0)777 553 1593

SOURCE Letter AI