Role
Design Manager
Timeline
Q1 – Q3 2023
The Challenge
As Design Manager for Search at Booking.com, I set out to transform how users discover and plan their trips. I saw an opportunity to unify our fragmented search experience into a cohesive system that would span across accommodations, flights, car rentals, and attractions.
My vision went beyond incremental improvements – I aimed to bridge the gap between the company’s near-term evolution and its long-term product vision by unlocking entirely new dimensions of search through trip types, themes, and events.
Recognizing the strategic importance of this initiative, I built support at the executive level, securing sponsorship from the Senior Director of UX to bring this vision to life.
The scope and ambition of the project attracted key stakeholders including Directors and Senior Directors of Product and Design, as well as the VP of Product – reflecting both its cross-functional nature and organizational impact.
Project Scope
This comprehensive project encompassed all search-related experiences, both implicit and explicit, across verticals.
The goal was to unlock new search dimensions — such as trip types, themes, and events — while creating a seamless experience for users regardless of the vertical. Our stakeholders included Directors and Senior Directors of Product and Design, as well as VP of Product.
| Phase | Timeframe |
|---|---|
| Discovery | Q1 ‘23 |
| Planning & Scoping | Q2 ‘23 |
| LT Sign-Off | Q2 ‘23 |
| Design Production | Q3 ‘23 |
| 2024 Planning | Q4 ‘23 |
Initial Research
Our research revealed several critical pain points:
- Repetitive Data Entry
Users had to enter the same preferences repeatedly across flights, accommodations, and attractions. This wasn’t just annoying – it created friction that prevented users from easily exploring different travel options. - Rigid Search Parameters
Traditional search was limited to destination, dates, and occupancy. This ignored the reality that many travelers start with broader ideas like “beach vacation” or “family-friendly city break.” - Disconnected Experiences
Each vertical (flights, accommodations, attractions) operated independently. This forced users to be their own travel agents, manually connecting different parts of their journey. - Limited Discovery
Users with broad travel intent struggled to explore options effectively. The system assumed everyone started with a specific destination in mind.
This fragmentation wasn’t just a design challenge – it was a strategic barrier to delivering on the “Connected Trip”, Booking.com’s ambitious company-level product strategy.
The “Connected Trip” aimed to transform how people experience travel by seamlessly connecting every aspect of their journey, and search would be the foundational layer enabling this transformation.
Guiding UX Discovery
I teamed up with our Principal Designer and brought in a Lead Designer from my team to lead our core team and an extensive group of stakeholders through workshops to define the core value drivers of our vision.
We facilitated rounds of ideation workshops and focus groups to explore new search capabilities, ensuring alignment on critical areas.
I led the team through a structured discovery process that combined multiple research streams:
- Market Analysis
Deep dives into competitor approaches and emerging travel tech trends - User Research Synthesis
Consolidating insights from multiple studies and data sources - Technical Exploration
Mapping existing search capabilities and identifying new opportunities - Stakeholder Interviews
Understanding priorities and constraints across departments
This multi-faceted approach ensured our vision would be both innovative and grounded in reality.
Delivering a Vision of Depth
To ensure depth, we leveraged research insights to define principles before starting design production:
- Anticipate user needs but keep users in control
- Help users shape trip intent in ways that work for them
- Enable transitions between broad and specific searches
- Adjust information density based on user intent
- Be intentional about when to inspire and when to inform
Drawing from our research, I saw an opportunity to radically reimagine how users discover and plan travel. While competitors focused on incremental improvements, we aimed to create a paradigm shift in travel search.
We crafted the vision narrative through three personas, each reflecting different ‘superpowers’:
- The Solo Traveller
Price-driven, leveraging conversational AI and unique search intents. - The Couple
Broad trip intent with preferences carried over. - The Family
Focused on safety and refinement through family profiles.
We explored a wealth of ideas through ideation workshops, embracing a diverging phase to uncover opportunities.
As our vision evolved, we honed in on three transformative concepts:
- Open Search
Users could express travel intent in their own words, breaking free from rigid forms. This addressed a key insight: people don’t think about destinations only – they think in experiences, feelings, and goals. - Multi-dimensional Browsing
A flexible system for exploring travel across multiple dimensions simultaneously. Users could seamlessly move between destinations, themes, activities, and vibes, reflecting how people naturally think about travel planning. - AI Trip Planner
Conversational guidance through the complex journey of trip planning. This wasn’t just about answering questions – it was about understanding context and providing personalized recommendations at the right moment.
Implementation Strategy
Early in the project, I noticed a pattern common to many large-scale initiatives: the initial excitement would give way to analysis paralysis as teams grappled with complexity.
To move from vision to reality and not lose momentum, I developed a phased approach that balanced ambition with practicality, and implemented several key processes:
- Sprint-like cycles
Short, focused work periods with clear deliverables, helping us maintain pace without sacrificing depth - Ongoing calibration
Quick check-ins focused on unblocking issues rather than status updates - Stakeholder reviews
Weekly sessions structured as working sessions rather than presentations, enabling real-time collaboration - Living documentation
Using Figma and Miro as collaborative spaces where ideas could evolve with input from all stakeholders
This hybrid approach combined the best of agile methodologies with the thoughtfulness required for strategic work.
Overcoming Challenges
The project faced several significant hurdles that required careful navigation:
Scope Complexity
With multiple verticals involved, each with their own priorities and technical constraints, alignment was crucial. I addressed this through:
- Clear communication channels
Establishing regular touchpoints with key stakeholders - Shared success metrics
Creating alignment around common goals - Early issue resolution
Regular reviews to identify and address concerns before they became blockers
Time Pressure
Throughout the project, we had to manage an accelerated timeline to inform strategic planning.
Rather than compromise quality, I adapted the approach:
- Restructured workflows
Prioritized high-impact deliverables without sacrificing thoroughness - Empowered team members
Delegated ownership of specific workstreams to trusted team members - Maintained quality
Implemented rapid feedback loops to ensure standards remained high
Impact & Results
The Search vision’s influence extended far beyond its immediate scope:
- AI Trip Planner
Directly shaped the development of Booking.com’s AI-powered planning experience - “Connected Trip” strategy
Our vision Informed the refinement of our company-level product strategy - Cross-department alignment
Influenced 2024 roadmaps across multiple departments
Jascha has struck a great balance in the project by providing proposals for review and steering. This approach has allowed the search team to move quickly while ensuring high-quality output at each step.
Principal Product Designer
Key Learnings
This initiative reinforced several crucial principles about leading transformative projects:
- Start with users
Ground ambitious visions in real user needs and behaviors - Enable the team
Create opportunities for growth while maintaining quality standards - Build alignment
Invest time in bringing stakeholders along on the journey - Stay adaptable
Be willing to adjust approaches based on feedback and constraints
The success of this initiative demonstrated that transformative change happens at the intersection of user needs, technical innovation, and strong cross-functional collaboration.
It set new standards for how we approach large-scale vision work while delivering tangible value to both users and the business.
Not only were you responsible for the end-to-end UX needs for the project, but you were also responsible for core elements of the project like facilitating check-ins, requirement gathering sessions between product/design/tech, defining working agreements, and collaboration models. Without your involvement the project could have easily spiralled into chaos.
Senior Engineering Manager