# Pierre-Olivier Lepage

> Pierre-Olivier Lepage is the CEO and co-founder of Cruisebound, a New York-based digital-first cruise booking platform he launched in 2022 after struggling to book his own first cruise online. A Polytechnique Montréal engineering graduate who earned dual MIT master's degrees in Transportation and Operations Research, Lepage previously built operations at Rocket Travel (a Booking Holdings company) and consulted at McKinsey before betting that the $66B cruise industry — where 80% of bookings still flow through travel agents — was ripe for a tech-native overhaul. Cruisebound has since raised $37.8M in total funding, serves customers averaging nine years younger than typical cruisers, and routes 42% of support queries through AI, positioning itself as the fastest-growing national online cruise agency.

- **Role:** CEO and Co-Founder at Cruisebound
- **Organizations:** Cruisebound, Rocket Travel (Booking Holdings), McKinsey & Company, MIT, Air Canada, Engineers Without Borders Canada
- **Nationality:** Canadian
- **Education:** Bachelor of Science, Industrial Engineering, Polytechnique Montréal, Master of Science, Transportation, Massachusetts Institute of Technology (MIT), Master of Science, Operations Research, Massachusetts Institute of Technology (MIT)
- **Known for:** Co-founded Cruisebound in 2022; grew it into one of the fastest-growing national online cruise agencies within three years, Raised $37.8M in total venture funding from top-tier travel tech investors, Attracted backing from former Booking Holdings CEO Jeff Boyd and Tripadvisor co-founder Steve Kaufer

## Career timeline

- **2009–2010** — Operations Research Analyst at Air Canada; built post-processing module to improve forecast accuracy
- **2010–2013** — Research Assistant at MIT; simultaneously earned dual master's degrees in Transportation and Operations Research
- **2012** — Summer Business Analyst at McKinsey & Company
- **2013–2015** — Business Analyst at McKinsey & Company; developed supply chain strategies
- **2015–2019** — Various roles at Rocket Travel (Booking Holdings): Senior Manager of Global Partnerships, Director of Partnerships, Senior Product Owner, Senior Director of Product
- **2019–2021** — Head of Business Operations at Rocket Travel (Booking Holdings)
- **2022** — Co-founded Cruisebound with Bjorn Larsen, Jay Hoffmann, and Tyler Barber
- **2023** — Raised $10M Series A led by Jeff Boyd (former Booking Holdings CEO) and PAR Capital Ventures; total raised $12.7M
- **2024-10** — Raised $13M Series B led by Thayer Ventures; total raised reaches $25.7M

## Achievements

- Co-founded Cruisebound in 2022; grew it into one of the fastest-growing national online cruise agencies within three years
- Raised $37.8M in total venture funding from top-tier travel tech investors
- Attracted backing from former Booking Holdings CEO Jeff Boyd and Tripadvisor co-founder Steve Kaufer
- Built platform aggregating 27,000+ global cruise itineraries across 19 major cruise lines
- Achieved 92% five-star Trustpilot ratings across thousands of reviews
- Engineered 83% self-serve booking rate, reducing dependence on agents
- Deployed AI chatbot handling 42% of all customer service requests
- Attracted customers averaging 9.5 years younger than the typical cruiser, expanding the market
- Achieved triple-digit revenue growth in the company's first two years
- Named to PhocusWire Hot 25 Travel Startups for 2026

## Latest updates

- **2024-10** — Closed $13M Series B round led by Thayer Ventures, bringing total funding to $25.7M
- **2024-10** — Cruisebound named to PhocusWire Hot 25 Travel Startups for 2026
- **2024-10** — Announced addition of travel industry veterans to leadership team
- **2025-11** — Participated in The Phocuswright Conference panel on AI in cruise technology

## Links

- Website: https://cruisebound.com
- LinkedIn: http://www.linkedin.com/in/pierreolivierlepage
- Twitter/X: https://twitter.com/cruiseboundinc
- Facebook: https://facebook.com/cruiseboundinc/

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Profile page: https://yespress.io/pierre-olivier-lepage
Published by YesPress — https://yespress.io
Last updated: 2026-06-12