Ali Akhtar

About Ali Akhtar

Ali Akhtar is the co-founder and CEO of Letter AI, an AI-native revenue enablement platform that helps sales teams ramp up faster with personalized training, coaching, and deal-level intelligence. Under his leadership, Letter AI has raised over $50 million in funding, including a $40 million Series B in February 2026, and serves Fortune 100 customers like Lenovo, Adobe, and Novo Nordisk.

Before founding Letter AI, Akhtar spent a decade in AI and ML across roles at McKinsey (as an AI-focused consultant), Samsara (Director of Engineering for Machine Learning), and project44 (VP of ML Products). It was his experience at Samsara — watching sellers constantly ping engineers for product knowledge rather than use expensive, low-adoption legacy enablement tools — that sparked the idea for Letter AI.

Career Highlights

• Co-founded Letter AI (originally Tractatus) through Y Combinator (W23 batch)
• Pivoted from AI developer tools to sales enablement during the YC batch, closing Lenovo as a customer before graduating
• Grew Lenovo deal 10x over two years
• VP of ML Products at project44
• Director of Engineering, Machine Learning at Samsara
• AI-focused consultant at McKinsey
• A.B. with Honors in Philosophy, Mathematics, Computer Science from University of Chicago

Notable Positions

On Why Legacy Enablement Fails

Akhtar’s core insight came from experiencing broken sales enablement firsthand:

“There’s this really expensive tool, which I couldn’t even get a license to because it was so expensive, that’s getting very low adoption. Sellers would say, ‘I can’t find anything in there. I barely log in.’”

He argues that legacy tools fail because they require armies of humans to curate content, while AI can automate personalization at a scale and speed that makes tools actually essential to sellers.

On AI-Native vs AI-Augmented

Akhtar draws a sharp distinction between adding AI features to existing software and building AI-native from scratch:

“With AI, you could actually tap into existing sources of knowledge and accelerate the process of highly personalized content development. Speed is what matters in today’s day and age.”

Key Quotes

• “If Letter disappeared, there would be a line of folks outside the door of the enablement team banging and asking for it to come back.” (on adoption)
• “Pre-Letter, an exercise like this would have taken them at least a month and tons of folks. With Letter, they were able to do it over a weekend with about two or three folks.” (on enterprise onboarding speed)

Related Reading

• Model Context Protocol (MCP) - Letter AI builds MCP servers for enterprise integration
• Agent2Agent Protocol (A2A) - Letter AI’s agent-to-agent communication
• SaaS-to-AI Transformation - The broader industry shift Letter AI exemplifies