The New York-based AI startup launches its proprietary Hamlet model, which delivers real-time guidance to sales representatives at Fortune 500 companies and other large enterprises.

The artificial intelligence startup Othello has raised $8 million in seed funding to expand its real-time AI sales coaching technology, designed to help sales representatives navigate customer conversations as they happen rather than analyzing performance after calls end.

The funding round included a16z speedrun, Owl Capital, and Long Journey Ventures, along with prominent technology entrepreneurs and executives. Angel investors include DoorDash co-founder Andy Fang, Ripple co-founder Chris Larsen, Hugging Face co-founder Thomas Wolf and Sentry co-founder David Cramer.

Founded by Jared Zelman and Raphael Assor, Othello is positioning its technology at the intersection of generative AI, enterprise sales productivity and real-time decision support.

Bringing AI Sales Coaching Into the Conversation

Othello’s powerful AI platform delivers actionable recommendations directly to sales representatives during live customer interactions.

The platform operates through a desktop application that overlays subtle prompts onto existing video conferencing and calling platforms without joining meetings as an additional participant.

Othello’s proprietary AI model Hamlet, is purpose-built for live sales conversations. According to the company, Hamlet generates contextual recommendations in under 500 milliseconds, letting representatives respond to changing conversations almost instantly.

The technology can identify missed discovery questions, recommend responses to objections, suggest relevant case studies and highlight opportunities to advance negotiations.

It also supports established sales methodologies, including MEDDPICC and Challenger, helping companies reinforce existing sales processes during customer interactions.

“There is a ton of technology before the conversation and way too much after it ends, but not a single tool that affects how you perform during the call,” said Jared Zelman, Othello’s co-founder and CEO.

“That’s not a software problem. It’s an AI problem. The only way to give smart recommendations in real time, with the full context of a deal, is to train AI models just for that.”

Enterprise Adoption Signals Growing Demand for Real-Time AI

Othello reports deployments at more than 50 large enterprises, including Fortune 500 organizations. Named customers include Microsoft, Capital One and Lyft.

Its customer base spans financial services, insurance, cybersecurity, healthcare, manufacturing, enterprise software and professional services.

Licensed sales representatives typically adopt the platform within one week of installation and use it during at least 95% of their calls.

Those company-reported adoption figures suggest that AI assistance integrated directly into daily workflows may face fewer adoption barriers. Other tools often require separate analysis or administrative activities.

Transformation of Sales

Othello’s emergence reflects a broader transformation in how businesses incorporate artificial intelligence into sales operations.

Gartner projects that by 2028, 60% of B2B seller work will be done through conversational user interfaces, up from less than 5% in 2023.

For enterprises managing complex sales cycles, real-time AI coaching offers several benefits. It could shorten onboarding periods, improve consistency, and give less-experienced representatives access to guidance previously available mainly through experienced managers.

Othello targets the critical moments when sales professionals must interpret customer needs, address concerns, and make decisions. Legacy systems automate administrative tasks.

$8 Million Investment Supports Othello’s Growth

The seed investment provides Othello with additional resources to advance its AI technology and expand its enterprise presence.

As businesses increasingly evaluate AI investments based on measurable productivity and revenue outcomes, Othello represents an emerging category of AI-powered tools that augment human performance rather than replace human interaction.

For sales organizations, Othello brings sophisticated coaching capabilities into the conversation at the exact moment they can influence the outcome.