Letter AI, an AI-native revenue enablement platform for enterprise go-to-market teams, has raised $40 million in a 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 round comes just four months after the company’s previous raise and reflects accelerating enterprise demand for AI-driven platforms designed to improve deal outcomes.
The new capital will be used to scale product development, expand Letter AI’s global team, and accelerate go-to-market efforts as enterprises move away from fragmented enablement tools toward unified, AI-native systems built for modern revenue teams.
The company positions itself at the forefront of what it describes as a fundamental reset in revenue enablement. Traditional platforms often rely on disconnected tools and static training libraries, contributing to low adoption rates and sellers spending less than 30% of their time with customers, according to Salesforce’s State of Sales 2024 report. In contrast, Letter AI was built as a unified system that integrates content, learning, coaching, and buyer engagement, delivering real-time, deal-specific intelligence tailored to each seller and opportunity.
Alongside the funding announcement, Letter AI introduced Letter Compass, a new product designed to deliver contextual, real-time guidance within active sales opportunities. By combining enablement content with live CRM data and customer interactions, Letter Compass embeds intelligence directly into the sales execution process.
Letter AI counts global enterprises such as Lenovo, Adobe, Novo Nordisk, Plaid, Zip, RingCentral, Kong, and SolarWinds among its customers, supporting revenue teams across more than 30 countries. Headquartered in Chicago, the company was co-founded by Ali Akhtar and Armen Forget and is backed by Battery Ventures and other institutional investors.
KEY QUOTES:
“Letter AI has changed how enablement shows up in our sales process. 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.”
Abdul Hakim, Executive Director, Digital Workplace Solutions, Lenovo
“Revenue enablement is a perfect problem for an AI-native platform because it sits at the intersection of content, people, and live decision-making. 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. What enterprises need is a holistic system that understands deal context and supports sellers throughout the lifecycle of a deal.”
Ali Akhtar, Co-Founder And CEO, Letter AI; Armen Forget, Co-Founder And CTO, Letter AI
“Revenue enablement is undergoing a fundamental reset. 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, Battery Ventures
“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. 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.”
Mark Roberge, Co-Founder, Stage 2 Capital; Founding CRO, HubSpot
