Tripadvisor

When I joined, TripAdvisor had an incredibly strong engineering culture. The company hired highly talented, capable people who were skilled not only technically but also in communication and teamwork. As a new engineer, it was almost intimidating to sit in meetings with such experienced colleagues. Expectations were high, but in a positive way. You felt pushed to grow, and over time you realized you belonged there and had the potential to meet that standard.

The general culture was excellent. Most colleagues were supportive, helpful, and genuinely invested in team success. It was a non-toxic, friendly environment built on mutual respect. Work life balance was solid, and management rarely pushed people to work beyond normal hours.

Although the tech stack was outdated when I joined, the company committed significant resources to modernizing it. By the time I left, the technical infrastructure had improved dramatically, which made everyday engineering work smoother and more efficient.

Career growth opportunities were strong. Salaries and benefits were competitive, the learning budget was generous, and professional development was encouraged. Remote flexibility was well supported, and managers were generally understanding of personal circumstances.

The COVID-19 pandemic devastated the travel industry, and TripAdvisor was hit especially hard. The layoffs that followed were massive and reshaped the engineering organization overnight. The company lost an enormous amount of talent, including many of the most experienced engineers and leaders who carried crucial domain knowledge. Morale collapsed, and a wave of voluntary departures continued for months afterward.

Since then, the company has never fully recovered. What used to be a cohesive culture gradually unraveled. Promotions came quickly for those who remained, but the lack of seasoned people to guide technical strategy became a long-term liability. Engineering depth and continuity suffered.

What followed was a long series of reorganizations. For years now, it has felt like the company reshuffles its structure once or twice every year. Reorgs became a running joke internally. Each one disrupted team focus, slowed productivity, and forced everyone to adapt to new priorities and leadership structures before the last changes had even settled.

There is also a huge operational cost to constant reorganization that often goes unacknowledged. Every reshuffle requires teams to rename themselves, recreate security groups, rebuild access structures, migrate permissions, reorganize Slack channels, update dashboards, adjust on-call rotations, reassign repos, and fix ownership mappings. Weeks of engineering time get spent on this instead of actual product work, and by the time things stabilize, another reorg is already looming.

Across multiple rounds of layoffs, the company continued losing some of its most capable and seasoned engineers. Many people who were central to the culture and success of the company either left voluntarily or were laid off based on cost considerations rather than performance. Watching some of the strongest colleagues walk out the door year after year felt surreal. The knowledge gaps widened, productivity slipped, and the once strong engineering identity faded.

Innovation stalled. Several new product attempts never gained traction, and large technical initiatives were abandoned mid-way at significant cost. Strategic direction became inconsistent, and communication from senior leadership often felt vague or misaligned across layers of the organization.

Meanwhile, the stock price declined to historic lows, reflecting the lack of a clear long-term strategy and growing market uncertainty.

TripAdvisor still has the foundations of a great company, but it cannot rebuild without stability. The constant cycle of layoffs and reorganizations has done long-term damage to morale, knowledge retention, and team cohesion. Leadership needs to commit to a clear, durable strategy and allow teams to focus without being reshuffled every few months.

Invest more in retaining top talent, rebuilding engineering depth, and supporting real innovation instead of reactive short-term adjustments. Improve communication from senior leaders so priorities are consistent across teams. Reduce reorg frequency and acknowledge the operational cost of each one.

There is still real potential here, but rebuilding trust will take time, investment, and a shift toward long-term thinking rather than constant restructuring.