Jared Zelman’s first sales pitch involved three slices of bread and two layers of ketchup. As a child, he sold ketchup sandwiches near his family’s summer home in New York, discovering that convincing someone to buy required more than the product itself. By high school, he was applying that instinct to a tutoring marketplace. He recruited students and overseas tutors to offer online sessions for $10 to $25 an hour, reaching customers through school flyers, academic events, and referral incentives. The business addressed two problems he saw in traditional tutoring: high prices and the difficulty of finding help when a student actually needed it.
Today, Zelman is working on another problem where timing matters. He is the co-founder and CEO of Othello AI, a New York company that helps salespeople navigate customer conversations as they happen. Its proprietary AI models, called Hamlet, suggest questions, responses to objections, and relevant product information during live calls. The company announced an $8 million seed round in October 2026, backed by a16z speedrun, Owl Capital, and Long Journey Ventures. Its premise is straightforward: preparation can help a salesperson enter a meeting, but the next question from a buyer may still demand knowledge or judgment they cannot immediately retrieve.
The idea emerged from Zelman’s experience selling his previous company, Cicero, which developed AI avatars for authors and podcasters. Struggling with enterprise sales calls, he enlisted a friend to hold up cue cards reminding him what to ask and say. The assistance improved his performance and became the starting point for Othello. In his telling, sales coaching becomes especially valuable when someone has to apply it under pressure. Reviewing a conversation afterward can reveal a missed opportunity, but it cannot recover the moment when a buyer needed a better answer.
Building that assistance requires both speed and context. Zelman says Hamlet can place a recommendation on a salesperson’s screen in approximately half a second. If a buyer mentions a competitor, for example, the system aims to suggest a response suited to the company and the conversation. Othello begins with general sales practices and learns from the customer’s own interactions, identifying approaches associated with positive responses and successful deals. “We’re able to see across every user, every sales rep in a company, what are the best things that they do,” Zelman said. “And we copy those things.” He acknowledges that learning those patterns requires substantial conversation volume and does not happen overnight.
Making the product useful inside established businesses required patient adaptation. Zelman describes Othello’s first major enterprise customer as a 150-year-old company with siloed operations and entrenched workflows. His team met with approximately 20 users each week for several months, adjusting the product around their needs. The experience gave the company a demanding environment in which to learn what employees would actually use. By the October interview, Zelman reported approximately 50 large enterprise customers, including Fortune 10 companies, with publicly traded businesses making up roughly half of its customer base.
For a product designed to help people persuade, Zelman also draws a firm boundary around accuracy. He rejects encouraging salespeople to promise capabilities they cannot deliver. “If you do not actually convey expectations accurately, they will be disappointed,” he said. His position is that Othello should guide representatives toward statements supported by what the company knows to be true. That makes the quality of its recommendations consequential beyond the immediate call: an answer that helps close a deal can still damage the relationship if it creates the wrong expectations.
With the new funding, Othello is investing in more individualized guidance and expanding its commercial team. Zelman says the goal is for the product to learn what each salesperson already knows and offer help where they need it. He also plans to hire 10 people across sales and marketing in New York, adding commercial capacity to a team he describes as predominantly engineers and researchers. The next stage will test whether Othello can deliver that assistance consistently across more organizations. For Zelman, the opportunity remains rooted in a familiar experience: knowing that a conversation matters and having the right idea arrive in time to use it.
