Otto Brings AI-Powered Personalization to Business Travel
Seattle startup Otto announced the wide release of its AI-powered travel assistant, Otto the Agent, on Thursday after nine months in closed beta. Founded by travel industry veterans and incubated at Madrona Venture Labs, Otto aims to revolutionize business travel by providing a personalized concierge-like experience that learns and adapts to individual preferences. The company’s mission strikes a balance between the efficiency of modern technology and the personalized service once provided by traditional travel agents.
Led by CEO Michael Gulmann, who spent nearly a decade at Expedia Group and worked at business travel management giant Egencia, Otto is designed to function like an exceptional executive assistant. The platform learns a traveler’s habits—from airline and hotel preferences to seat choices and loyalty programs—even accounting for nuanced needs like avoiding rooms with train noise or finding hotels with rooftop bars. This eliminates the typical “endless scroll” experience by instantly surfacing the best options tailored to each user. Unlike general AI tools that merely direct users to external booking sites, Otto manages the entire transaction process within its interface, handling bookings, cancellations, rebookings, and credit management seamlessly. The assistant can also proactively detect upcoming trips by connecting to a user’s calendar and suggest appropriate itineraries before being asked.
The technology has already impressed early adopters like Barney Harford, former CEO of Orbitz Worldwide and former COO of Uber, who described Otto as “a glimpse into the future” after using it for several months. Harford, who is also an investor in the company, praised how Otto has simplified his booking process down to just minutes by learning his business travel preferences. The platform currently focuses on flights and hotels, but Gulmann indicated that car rentals and dinner reservations are on the horizon—services that would typically be handled by an executive assistant. “The reality is, most people don’t have an EA,” Gulmann noted, adding that part of Otto’s inspiration came from his own positive experiences with an executive assistant during his time at Expedia.
Otto is being offered free to individual business travelers and small to mid-sized businesses for the next 12 months, with the company generating revenue through commissions. Through a strategic partnership with travel management company Direct Travel, Otto is launching pilot programs with two unnamed companies. Direct Travel, which was acquired by Madrona and others in April 2024, also invested in Otto’s seed round. Steve Singh, managing director at Madrona who co-founded business expense software giant Concur, serves as executive chairman of Otto, adding significant industry expertise to the startup’s leadership. Since leaving Concur after its $8.3 billion acquisition by SAP in 2014, Singh has taken on executive chairman roles at several travel and expense management companies, including Spotnana, Center, and Troop.
Despite entering a competitive field with both startups and incumbents developing AI-powered travel tools, Gulmann is confident in Otto’s approach and development pace. “It’s insanely faster to develop and to build the product,” he said, noting that Otto’s 10-person team is achieving impressive results despite being much smaller than established industry giants like Expedia or Booking.com. The CEO admitted that returning to travel innovation was “the last thing he thought he’d get back into,” but recognized that the landscape has changed dramatically since online travel agencies first disrupted human travel agents in the 1990s.
Otto represents a fascinating evolution in the travel industry—a return to the personalized service model of traditional travel agents, but powered by cutting-edge AI technology. This hybrid approach addresses a gap in the current business travel experience, where efficiency often comes at the cost of personalization. As business travel continues to recover post-pandemic, Otto’s timing may prove opportune for travelers seeking both convenience and customization. The platform’s ability to learn individual preferences while handling the entire booking process could potentially disrupt the business travel sector in the same way online booking sites transformed leisure travel decades ago. With backing from industry veterans and a focus on creating an assistant-like experience accessible to all business travelers, Otto is positioning itself at the intersection of AI innovation and travel expertise—potentially changing how professionals plan, book, and manage their business journeys.
