Power plays, culture clashes, and the hidden costs of success at one of Europe’s most secretive tech empires
May 28, 2025
Behind the polished facade of Booking.com’s global success lies a story of internal power struggles, cultural clashes, and controversial practices. In The Machine, three Dutch journalists peel back the curtain on the Amsterdam headquarters and reveal the human dramas that shaped the company – from executive firings and clandestine affairs to burnout-fueled booze-fests and covert data breaches. Drawing on extensive reporting and Booker Holdings’ own fact-checking, the book chronicles Booking.com’s rise from a scrappy Netherlands startup to the world’s leading hotel-booking platform, while exposing the tensions and tactics that drove its meteoric growth.
Key takeaways
- High-profile CEO firings and forced esignations
- Gillian Tans, a founding “Dutch Mafia” member, was abruptly fired as Booking.com CEO on June 20, 2019, amid concerns over stagnating growth, cultural lethargy, and insufficient cooperation with sister brands.
- Earlier, in April 2016, Darren Huston resigned as Priceline Group CEO following an undisclosed affair with an Agoda employee, highlighting the company’s opaque ethics enforcement.
- Insular culture and brand autonomy
Booking.com fiercely guarded its autonomy, resisting resource- and data-sharing with sister brands (Priceline, Agoda, Kayak), fearing dilution of its identity – even as Booking Holdings leadership pushed for greater integration. - Local backlash and public scrutiny
- The company leveraged Netherlands’ Innovation Tax credit to save an estimated $2.5 billion over a decade, and during the pandemic accepted substantial state aid (€100 billion total across Europe) while cutting jobs and awarding multimillion-dollar bonuses – sparking public outrage.
- Booking Holdings later repaid roughly $156 million of pandemic relief funds, framing the aid as a measure to preserve employment.
- Aggressive marketing tactics
Booking.com’s “only X rooms left” and “last booked X minutes ago” messaging drove urgency – often with hotels gaming the system by limiting feed of available rooms, practices now curbed by UK and EU competition agreements. - Undisclosed security breach
In early 2016, a security team member uncovered that a U.S.-based intruder had siphoned customer PINs for reservation changes – an intrusion suspected to involve U.S. intelligence – but Booking.com opted not to notify regulators or customers, citing no credit-card data loss and no legal requirement. - Outdated technology stack
Despite its self-branding as a tech powerhouse, until at least 2019 Booking.com ran its original booking engine and relied heavily on Perl – discouraging newer developers and symbolizing technical debt. - Pervasive A/B testing culture
The company ran up to 1,000 simultaneous A/B tests, with employee rewards tied to results – fostering a bonus-driven environment where some testers inflated metrics to secure promotions. - Foundational leadership of Kees Koolen
Though often overshadowed by later CEOs Jeffery Boyd and Glenn Fogel, Kees Koolen (CEO 2008–2011) introduced a metrics-driven rigor and search-marketing strategy that laid critical groundwork for Booking.com’s dominance.
Get the full story at yahoo! finance and the book at Lebowski Publishers
