Letter AI Raises $40M Series B, Launches Deal-Level Enablement Tool

Key Takeaways

• Letter AI raised $40 million just four months after closing a $10.6 million Series A.
• The new Compass product embeds AI-driven coaching into live CRM workflows.
• Investors are backing AI-native revenue infrastructure as measurable sales ROI becomes clearer.

Letter AI announced on Feb. 24, 2026, that it raised a $40 million Series B funding round led by Battery Ventures. Existing investors Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital and Formus participated in the round.

Alongside the funding, the company launched Letter Compass, a product that, according to company officials, integrates enablement content and training with live CRM data to deliver deal-specific guidance to sellers, customer success managers and sales engineers.

Table of Contents

• Letter Compass Feature Breakdown
• From Series A to B in 120 Days
• The New Standard: CRM-Native Intelligence
• Letter AI Background

Letter Compass Feature Breakdown

Rather than offering static enablement materials, Letter Compass operationalizes CRM data into deal-specific action. Its core functionality breaks down into the following components:

Feature	How It Works
Deal-specific coaching	On-demand guidance tuned to individual deal dynamics
Personalized messaging	Customer-specific content matched to sales stage
Curated content	Materials selected for specific contacts and accounts
Sales agent insights	AI-driven recommendations aimed at deal advancement

From Series A to B in 120 Days

Letter AI has moved aggressively to establish itself in the AI-native revenue enablement market, closing nearly $51 million across two rounds in four months. In October 2025, the company announced a $10.6 million Series A led by Stage 2 Capital. The round brought Mark Roberge, founding CRO of HubSpot and co-founder of Stage 2 Capital, onto the board. The company reported 15× customer growth over the prior year, citing enterprise accounts including Lenovo, Adobe, Novo Nordisk, Plaid, Zip, Kong and SolarWinds.

Four months later, Letter AI secured a $40 million Series B led by Battery Ventures, with CEO Ali Akhtar reporting the post-money valuation now sits in the hundreds of millions. Battery Ventures partner Brandon Gleklen joined the board.

The New Standard: CRM-Native Intelligence

Modern revenue enablement platforms integrate deeply with CRM systems to surface contextual intelligence at the point of sale.

Microsoft Copilot implementations showcase that impact: Lumen reduced seller research time from four hours to 15 minutes per deal by automating past interaction summaries and next-step recommendations, projecting $50 million in annual time savings.

Enterprise CRM expectations have also expanded beyond pipeline tracking. Organizations now desire platforms that anticipate customer needs and coordinate action across the customer lifecycle through predictive insights, journey orchestration and real-time recommendations.

Conversational Co-Pilots & Content Decisioning

Conversational AI in sales environments guides discovery, explains options and helps complete transactions through natural dialogue. These systems access product data, inventory and order status in real time.

The interfaces work alongside analytics to deliver AI-powered content decisioning that adapts engagement strategies based on individual behavior.

Organizations deploying AI-powered analytics and automation reported up to 25% increases in customer satisfaction and significant operational cost reductions. Additionally, a McKinsey analysis found that 63% of companies embedding AI into sales achieved at least 5% revenue uplift.

Letter AI Background

Letter AI is a generative AI-powered revenue enablement platform founded in 2023, serving mid-market and enterprise B2B organizations. The platform consolidates content creation, training, coaching and deal management into a single system.