In a world where countless business professionals juggle complex travel schedules, Otto has tapped into a growing market need that resonates with many entrepreneurs like myself. Launched officially in December 2025, its promise is quite straightforward: an artificial intelligence agent that acts as your virtual executive assistant, designed to simplify business travel. This is no small feat in an industry where efficiency and personalization matter more than ever.
Michael Gulmann, Otto's founder and a recognized name in the travel sector thanks to his years at Expedia and Egencia, leads the way. His focus is crystal clear, build a product that understands and anticipates travel needs the way a top executive assistant would. It's a service not just for executives at large firms but often for those running smaller businesses or startups, who could never realistically hire someone for that role.
One of the most interesting aspects for me is realizing that Otto isn’t trying to disrupt the entire world of corporate travel. Instead, it has chosen to fill a significant gap, those professionals and businesses too small for traditional travel management services like Concur or companies that can’t justify the cost of an assistant. The idea is to deliver an elite service, one usually reserved for senior managers, directly to your smartphone. Let’s unpack its features, explore how it works, and determine how entrepreneurs like us can take advantage of this tool.
Otto’s Features That Make It Stand Out
Otto’s core strength is its uncanny ability to tailor every part of your travel experience. It goes beyond booking flights and hotels. Here’s how:
-
Full Personalization
Otto remembers your preferences in unbelievable detail. Do you always prefer aisle seats on flights? Does Wi-Fi speed in your hotel matter more than its location? Otto learns these nuances quickly. This personalization is perfect for founders, especially those pitching to investors across the globe and jumping time zones with little notice. -
Proactive Planning
Otto syncs directly with your calendar, ensuring nothing gets overlooked. Say you're flying out on a Tuesday morning for meetings in London. Otto will flag flights, propose itineraries, and even remind you about airport check-in times in a neatly packaged notification. It’s the right dose of hand-holding for overworked entrepreneurs. -
Problem-Solving on the Go
Business travelers know the pain of delayed flights or sudden cancellations. Otto steps in like a dedicated EA, rebooking flights or finding alternatives without requiring you to scroll airline websites. This feature can potentially save hours, rooting out unnecessary distractions. -
Entire Lifecycle Coverage
From pre-planning the trip to managing disruptions during travel and even handling post-trip expense reports, Otto keeps it all centralized and user-friendly. As a founder who frequently neglects admin tasks post-travel, I find this all-encompassing approach particularly helpful.
How to Make the Most of Otto
If Otto has piqued your curiosity, integrating it into your workflow is not only simple but also logical. Here’s what I recommend:
-
Start by Linking Your Calendar and Loyalty Accounts
Otto thrives on data, and the more it knows, the smarter it gets. Connecting your email, calendar, and frequent flyer programs ensures that every interaction becomes sharper and more meaningful. -
Experiment with Small Trips First
Before relying on this AI for major international deals or investor gatherings, test it out with domestic trips or less time-sensitive meetings. This helps you notice how effectively it reacts to changes. -
Rely on It for Emergency Management
One area where Otto truly outshines is how it manages on-the-fly changes. Use this to handle last-minute flight hiccups or unexpected cancellations, leaving you free to focus on critical meetings or pitch presentations.
Common Mistakes to Avoid as an Entrepreneur when Using Otto
While Otto can make travel easier, there are a few pitfalls users should steer clear of:
-
Over-reliance on Automation
Otto, like any AI, isn't infallible. Keep a manual backup or an alternative plan, especially for critical business engagements. -
Ignoring Pre-Trip Checklists
Otto is designed to handle complex itineraries, but you still need to double-check certain features like seat preferences or double-booked calendar slots before confirming. -
Failure to Maximize Loyalty Programs
Have loyalty accounts with airlines or hotel chains? Otto can leverage these for better deals, but only if you actively enable these features during profile setup.
Entrepreneur Insights
From a strategic point of view, Otto is leveraging one of the foundational ideas of AI, choosing a niche with deeply specific pain points and resolving them with precision. It sidesteps the broad approach so many tools attempt and zeros in on specialized needs, akin to hiring a niche consultant instead of a generic business advisor.
This resonates with me as I manage startups across different regions. Having access to Otto means minimizing the slog of endless travel comparison websites and focus-shifting delays. On-the-go decision-making becomes much leaner, something every entrepreneur should value.
Another fascinating element is Otto’s team and backing. The involvement of experienced travel tech veterans like Steve Singh, a name synonymous with Concur and SAP, underpins the professionalism of this product. Madrona’s support further confirms they’re working to create a foundational company in this space, not just another startup experiment.
Final Thoughts
Otto has emerged as an interesting solution for the business traveler, focusing not just on time savings but quality of experience. Its roots in Seattle, combined with its leadership’s impressive track record, signal this isn’t any ordinary travel AI, it’s one built for heavy users who depend on reliability as much as convenience.
As entrepreneurs, adopting tools that reduce mental clutter is key. Otto isn’t revolutionizing how founders manage travel, but it’s a welcome step for those who aim to streamline day-to-day chaos while staying productive globally. If you’re tired of the constant disruption that travel brings, Otto’s offering might just be one of the most practical additions to your toolkit this year.
For more details about the company or to try it yourself, visit the Otto travel assistant website. As always, I’ll be testing it on my next big pitch meeting in Paris. Let’s see if Otto can help me arrive on time and stress-free. If it happens, you might see me writing a fan letter to this digital assistant sooner than later.
FAQ
1. What is Otto and how does it work?
Otto is an AI-powered travel assistant that mimics an executive assistant, helping business travelers manage their trips end-to-end, including planning, booking, and handling disruptions. Explore Otto’s Features
2. Who founded Otto and what experience do they have?
Otto was founded by Michael Gulmann, a former Expedia executive with over 10 years of leadership experience in travel technology. Learn about Michael Gulmann
3. How does Otto personalize travel experiences?
Otto learns user preferences, such as seat choices, hotel locations, and loyalty programs, to create hyper-personalized itineraries. Discover Otto’s Personalization
4. What happens if travel disruptions occur while using Otto?
Otto handles cancellations, rebookings, and other changes proactively, ensuring seamless travel for its users. Learn how Otto Manages Disruptions
5. What makes Otto different from other corporate travel tools?
Otto targets SMBs and solo professionals who cannot afford traditional travel management services, providing a high-touch personalized experience at a lower cost. Understand Otto’s Unique Niche
6. Who is backing Otto financially and strategically?
Otto has received investment and guidance from Madrona Ventures, as well as notable industry players like Steve Singh, co-founder of Concur. Learn about Otto’s Investors
7. Does Otto integrate with calendars and loyalty programs?
Yes, Otto syncs with user calendars and leverages loyalty programs to provide streamlined travel booking and management. See Otto’s Features
8. What is Otto’s pricing model?
Otto is free for individuals and SMBs for the first 12 months, generating revenue through travel commission fees. Learn about Otto’s Pricing
9. What is Otto’s target audience?
Otto is built for SMBs and busy professionals who need executive-level travel support without hiring a full-time assistant. Discover Otto’s Target Market
10. How does Otto manage an entire trip lifecycle?
Otto handles everything from planning and booking to managing disruptions mid-trip and expense reporting afterward, centralizing all tasks in one tool. Explore Otto’s Lifecycle Features
About the Author
Violetta Bonenkamp, also known as MeanCEO, is an experienced startup founder with an impressive educational background including an MBA and four other higher education degrees. She has over 20 years of work experience across multiple countries, including 5 years as a solopreneur and serial entrepreneur. Throughout her startup experience she has applied for multiple startup grants at the EU level, in the Netherlands and Malta, and her startups received quite a few of those. She’s been living, studying and working in many countries around the globe and her extensive multicultural experience has influenced her immensely.
Violetta Bonenkamp's expertise in CAD sector, IP protection and blockchain
Violetta Bonenkamp is recognized as a multidisciplinary expert with significant achievements in the CAD sector, intellectual property (IP) protection, and blockchain technology.
CAD Sector:
- Violetta is the CEO and co-founder of CADChain, a deep tech startup focused on developing IP management software specifically for CAD (Computer-Aided Design) data. CADChain addresses the lack of industry standards for CAD data protection and sharing, using innovative technology to secure and manage design data.
- She has led the company since its inception in 2018, overseeing R&D, PR, and business development, and driving the creation of products for platforms such as Autodesk Inventor, Blender, and SolidWorks.
- Her leadership has been instrumental in scaling CADChain from a small team to a significant player in the deeptech space, with a diverse, international team.
IP Protection:
- Violetta has built deep expertise in intellectual property, combining academic training with practical startup experience. She has taken specialized courses in IP from institutions like WIPO and the EU IPO.
- She is known for sharing actionable strategies for startup IP protection, leveraging both legal and technological approaches, and has published guides and content on this topic for the entrepreneurial community.
- Her work at CADChain directly addresses the need for robust IP protection in the engineering and design industries, integrating cybersecurity and compliance measures to safeguard digital assets.
Blockchain:
- Violetta’s entry into the blockchain sector began with the founding of CADChain, which uses blockchain as a core technology for securing and managing CAD data.
- She holds several certifications in blockchain and has participated in major hackathons and policy forums, such as the OECD Global Blockchain Policy Forum.
- Her expertise extends to applying blockchain for IP management, ensuring data integrity, traceability, and secure sharing in the CAD industry.
Violetta is a true multiple specialist who has built expertise in Linguistics, Education, Business Management, Blockchain, Entrepreneurship, Intellectual Property, Game Design, AI, SEO, Digital Marketing, cyber security and zero code automations. Her extensive educational journey includes a Master of Arts in Linguistics and Education, an Advanced Master in Linguistics from Belgium (2006-2007), an MBA from Blekinge Institute of Technology in Sweden (2006-2008), and an Erasmus Mundus joint program European Master of Higher Education from universities in Norway, Finland, and Portugal (2009).
She is the founder of Fe/male Switch, a startup game that encourages women to enter STEM fields, and also leads CADChain, and multiple other projects like the Directory of 1,000 Startup Cities with a proprietary MeanCEO Index that ranks cities for female entrepreneurs. Violetta created the "gamepreneurship" methodology, which forms the scientific basis of her startup game. She also builds a lot of SEO tools for startups. Her achievements include being named one of the top 100 women in Europe by EU Startups in 2022 and being nominated for Impact Person of the year at the Dutch Blockchain Week. She is an author with Sifted and a speaker at different Universities. Recently she published a book on Startup Idea Validation the right way: from zero to first customers and beyond, launched a Directory of 1,500+ websites for startups to list themselves in order to gain traction and build backlinks and is building MELA AI to help local restaurants in Malta get more visibility online.
For the past several years Violetta has been living between the Netherlands and Malta, while also regularly traveling to different destinations around the globe, usually due to her entrepreneurial activities. This has led her to start writing about different locations and amenities from the POV of an entrepreneur. Here’s her recent article about the best hotels in Italy to work from.
About the Publication
Fe/male Switch is an innovative startup platform designed to empower women entrepreneurs through an immersive, game-like experience. Founded in 2020 during the pandemic "without any funding and without any code," this non-profit initiative has evolved into a comprehensive educational tool for aspiring female entrepreneurs.The platform was co-founded by Violetta Shishkina-Bonenkamp, who serves as CEO and one of the lead authors of the Startup News branch.
Mission and Purpose
Fe/male Switch Foundation was created to address the gender gap in the tech and entrepreneurship space. The platform aims to skill-up future female tech leaders and empower them to create resilient and innovative tech startups through what they call "gamepreneurship". By putting players in a virtual startup village where they must survive and thrive, the startup game allows women to test their entrepreneurial abilities without financial risk.
Key Features
The platform offers a unique blend of news, resources,learning, networking, and practical application within a supportive, female-focused environment:
- Skill Lab: Micro-modules covering essential startup skills
- Virtual Startup Building: Create or join startups and tackle real-world challenges
- AI Co-founder (PlayPal): Guides users through the startup process
- SANDBOX: A testing environment for idea validation before launch
- Wellness Integration: Virtual activities to balance work and self-care
- Marketplace: Buy or sell expert sessions and tutorials
Impact and Growth
Since its inception, Fe/male Switch has shown impressive growth:
- 5,000+ female entrepreneurs in the community
- 100+ startup tools built
- 5,000+ pieces of articles and news written
- 1,000 unique business ideas for women created
Partnerships
Fe/male Switch has formed strategic partnerships to enhance its offerings. In January 2022, it teamed up with global website builder Tilda to provide free access to website building tools and mentorship services for Fe/male Switch participants.
Recognition
Fe/male Switch has received media attention for its innovative approach to closing the gender gap in tech entrepreneurship. The platform has been featured in various publications highlighting its unique "play to learn and earn" model.