Ali Akhtar

A philosophy major who learned to sell software, then taught software to sell

Ali Akhtar runs Letter AI, an AI-native revenue enablement platform out of Chicago. In February 2026 it raised a $40 million Series B led by Battery Ventures. The thing it sells is deceptively simple: the coaching a salesperson wishes they had, delivered the moment a deal is live.

Letter AI is not a content library with a chatbot stapled to the side. Akhtar's pitch is that enablement - the unglamorous machinery of training reps, organizing collateral, and coaching deals - is the rare corporate problem that an AI-native system was practically designed for. It sits at the seam where company knowledge, human behavior, and split-second decisions all meet. Legacy software handled the first part and ignored the rest. Letter AI tries to hold all three at once.

The company counts Lenovo, Adobe, Novo Nordisk, Plaid, Zip, RingCentral, Kong, and SolarWinds among its customers, with revenue teams spread across more than thirty countries. For a company that came out of Y Combinator's Summer 2023 batch, that is a steep climb in a short window.

The itch he couldn't stop scratching

Before Letter AI, Akhtar and co-founder Armen Forget spent their careers building AI software for enterprise customers - Akhtar leading machine learning and product teams, Forget architecting the backends underneath them. They worked at companies like Samsara and Cirrus Logic, close enough to the revenue org to see a pattern repeat: a strong product, a capable seller, and a deal that slipped because the seller couldn't get the right answer at the right moment. Poor enablement, quietly, was costing real money.

So they built the tool they wished their own teams had. That origin matters. Letter AI is not a market a founder spotted from the outside and decided to attack. It is a frustration two builders lived through and refused to keep living with.

The conviction shows up in how Akhtar talks about the incumbents. He describes legacy tools as built for static libraries and periodic training - shelves of PDFs and a quarterly workshop - in a world where sellers need guidance that is personalized, contextual, and available in the exact minute a deal is happening. The gap between those two pictures is the whole company.

Four careers, stacked

Read Akhtar's resume and you find at least four different people. There is the consultant: an engagement manager at McKinsey & Company, learning how large organizations actually decide things. There is the operator on a presidential campaign, working in product around the Obama effort, where the customer is a voter and the deadline is non-negotiable. There is the machine learning leader who directed data and ML engineering at Samsara and ran data and ML product at project44. And there is the founder, who co-founded Statum Positioning Systems before Letter AI.

That range is unusual. Most AI founders are engineers who learned business reluctantly, or business minds who hire the engineering. Akhtar is described, fairly, as someone who can run a P&L and ship an ML model - the technical depth to build the thing and the commercial fluency to know what to build. The academic foundation reads the same way: an honors degree from the University of Chicago in philosophy, mathematics, and computer science, then an MBA with high distinction from Michigan's Ross School, with a focus on data science and business strategy.

Philosophy and machine learning are not the strange pairing they look like. Both are, at heart, about how knowledge gets represented and turned into a decision. Letter AI is a company built on exactly that question: how do you take what an organization knows and put it in a seller's hands at the moment of choice?

Letter Compass and the moment of the deal

Alongside the Series B, Akhtar's team launched Letter Compass, the clearest expression yet of the thesis. Where the broader platform helps teams build training, content, and coaching faster, Compass narrows the focus to a single live opportunity. It fuses enablement content and learning with real CRM data and actual customer interactions, then hands the seller deal-specific guidance for the opportunity in front of them - not generic best practice, but a read on this account, this buyer, this stage.

That is the difference between a search box and a colleague who has read every deal you have ever run. Akhtar frames it plainly: enablement always had the right mission - help revenue teams win more, win better, win faster. What it lacked was a system that could deliver on the promise in real time. Compass is the attempt to close that loop.

The money, and who put it in

The $40 million Series B arrived in February 2026, roughly four months after the prior round - fast even by the compressed clock of AI funding. Battery Ventures led, with Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and existing backers joining. Total funding now sits above $52 million. The cap table is a tell: Stage 2 Capital is run by go-to-market operators, and a roster like this signals belief from the exact people who would know whether an enablement product actually moves revenue.

Why Chicago, and why it matters

Letter AI is headquartered in Chicago. In a field that treats a 415 area code as table stakes, that is a small act of defiance. It also fits Akhtar's story neatly - his degree, and a chunk of his career, are rooted in the city. Building a serious AI company there is a quiet argument that the talent and the customers do not all live on one coast.

In his own words

The bet

Akhtar's wager is that the future of selling looks less like a binder and more like a coach in your ear - one that knows the product, the playbook, and the specific human on the other end of the call. He has the parts to make that argument credible: the engineering to build the model, the operating scars to know where deals really break, and a co-founder who has spent his life in the backends that make it run. Whether enablement becomes the system of record for how revenue teams learn and sell is still unwritten. But it is a rare founder who has been the consultant, the operator, the ML director, and the buyer of the very tool he now sells. Akhtar has been all four.

Founder Firesides with YC

YC General Partner Diana Hu sits down with Ali Akhtar and co-founder Armen Forget to talk through how Letter AI was built and where AI-powered revenue is headed.

▶ AI-Powered Revenue is Here - watch on YouTube