Letter AI
Letter AI sells generative AI tools for sales teams to create training materials and practice demos faster. The Chicago-based startup has 61 employees and raised $55 million in a Series B round in February 2026.
The growth story
Letter AI grew from 1 to 61 employees between 2022 and 2026, raising $55M along the way, most recently a Series B in February 2026.
About
Letter AI provides software that uses generative AI to help sales teams quickly produce training content, customize materials for specific customers, and practice product demonstrations. Its tools aim to speed up the creation of sales collateral and coaching simulations.
The company was founded in 2023 and has grown to 61 employees. It raised $55 million in a Series B round in February 2026, backed by investors including Battery Ventures and Lightbank.
Founders and leadership
Engineering is the largest function with 20 employees, about a third of the company. The leadership team spans Chicago, where the company is headquartered.
The Letter AI org chart
Ali Akhtar (Founder & CEO) leads 15 mapped leaders with 2 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 19 (+217% YoY), Sales 11 (+450% YoY), Customer Success and Support 8 (+167% YoY), Business Development 3 (+50% YoY), Operations 3 (+200% YoY).
Talent flow
Employees come from companies like project44, Salesforce, and Samsara, with project44 being the top source of hires. Alumni have moved to roles at DoorDash, Dubai Holding, and smaller tech firms.
Most common previous employers of Letter AI staff: project44 (5), LinkedIn (3), Salesforce (2), Samsara (2), Docusign (2), The Coca-Cola Company (2). Former Letter AI employees most often moved to DoorDash (1), Sprocket Sports (1), Dijkstra Tech (1), Pine Technologies Pvt (1), Dubai Holding (1), SMB Team (1).
Alumni worth knowing
Web traffic
Traffic mix: 71% direct, 19% search, 2% social, 0% paid.
What this company is made of
Most common skills at Letter AI: Leadership (25), Python (Programming Language) (23), JavaScript (21), Microsoft Excel (21), Public Speaking (20), Microsoft Office (20), Communication (20), React.js (18).
Where the team actually sits
Letter AI people are concentrated in Illinois, United States (23), California, United States (15), Greater Chicago Area (4), San Francisco Bay Area (4). 2 offices on record.
Search footprint
Letter AI attracts about 28 organic search visits a month, traffic worth roughly $0K a month if bought through ads. It gained 60 ranking keywords and lost 8 in the last period.
Frequently asked
Letter AI has 61 employees as of September 2026.
Letter AI has raised $55M in total, most recently a Series B round in February 2026.
Letter AI was founded in 2023 by Armen Forget, Ali Akhtar.
Ali Akhtar (Founder & CEO) sits at the top of Letter AI's reporting structure, with 2 direct reports.
The most common previous employers of current Letter AI staff are project44 (5 people), LinkedIn (3 people), Salesforce (2 people).
Former Letter AI employees most often move to DoorDash (1), Sprocket Sports (1), Dijkstra Tech (1).
Letter AI attracts about 28 organic search visits a month, worth roughly $0K a month in equivalent ad spend.
The most common skills among Letter AI staff are Leadership, Python (Programming Language), JavaScript, Microsoft Excel, Public Speaking.
Letter AI staff are concentrated in Illinois, United States (23), California, United States (15), Greater Chicago Area (4).
Letter AI has about 19 people in Engineering, up 217% over the past year, as of September 2026.
Letter AI has about 11 people in Sales, up 450% over the past year, as of September 2026.
Computed from 51 current and 9 former Letter AI profiles, as of September 2026. Source: Crustdata.
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