Group
Bookings
Group
Bookings
Platform
Web & app
Team
1 PD 👋, 1 UX Writer, 1 MM,
2 PM, 4 Eng.
1 PD 👋, 1 UX Writer,
1 MM, 1 PM, 4 Eng.
Timeline
Nov 2025 - Jan 2026
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Headout is a global online managed marketplace for instantly booking local experiences, tours, and attractions, helping travelers reduce the complexity in making choices.
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Claustrophobia!
How I tried to simplify Headout group booking experience to improve Select to Checkout conversion
How I tried to simplify Headout group booking experience to improve Select to Checkout conversion
Timeline
A rough estimation of the project timeline. It is still on-going
Background
Since the African market is primarily driven by group experiences, we tailored the UX to match this behavior. Even with limited initial inventory, the focus was on proactively optimizing the user journey for the region's specific needs.
A regular experience
As a managed marketplace, Headout clubs similar experiences together, so that user’s have a narrowed decision making process.
A group experience
Group bookings come in various types and pax sizes based on the vendor, hence the regular approach did not fit well here.
Group types
All the group bookings that we list can be classified into 3 major brackets.
1. One price for all
In this tier, the pricing is independent of group size, meaning the fee remains constant for any selection up to the predefined maximum headcount cap.
2. Sets of groups
This variation utilizes range-based pricing, clustering users into sets like 1-4 pax. The price is locked for any number within a set, stepping up incrementally only as the group expands into a higher bracket.
3. Price increments
In this model, every additional passenger triggers only a marginal increment in the total price. This structure effectively drives down the per-pax cost as the group size expands.
Metrics indicated a severe drop-off in the funnel, with Group bookings converting 20x lower than the General booking.
The root cause.
Users are primarily price-conscious, and the group label is viewed as Secondary noise over the final cost.
But...
The current group pricing was too constrained and unclear, and people thought that the tours were overpriced and missed on the savings, which dorpped the CVRs.
Group based pricing division
General booking - visitor to order flow conversion
Group booking - visitor to order flow conversion
The sticker shock effect
The funnel showed a sharp dip post-selection because our pricing failed the competitive comparison test. By displaying lump-sum totals in a market accustomed to per-head pricing, we inadvertently signaled an inflated price point.
Brainstooooorming.
Over a two-week design sprint, we explored 20+ distinct iterations. We prioritized the three strongest iterations that best aligned with user logic.
Brain storming session with the PM (& my mentor)
01. Unified pricing
Validation
We tested an 'Education-First' approach to transparency. However, validation data showed this backfired: the sticker price remained high, and the cognitive burden of calculating per-person savings caused users to abandon the funnel.
02. 2 Different Approaches
Validation
Our intent was to build trust by mirroring the checkout pricing early in the flow. Yet, validation confirmed this information density had an inverse effect—overwhelming users and obscuring the value proposition instead of aiding it.
03. Unified pricing + Configurable number
Configurable number
The default ticket count is initialized at 3, reflecting the highest frequency booking size. However, this parameter is fully configurable, allowing business teams (BDMs) to adjust the default value dynamically based on changing market behaviors.
Validation
We decluttered the interface to focus on value, maintaining only a necessary pricing disclaimer. The design now consistently utilizes ‘per-guest’ pricing, a pattern that aligns with user mental models and has been statistically proven to drive higher efficiency.
We finalized on Config. Number
The reasoning
While the other ideations solved for the purpose, user testing revealed that aggregate costs caused sticker shock and forced mental math. We prioritized UX over engineering effort, restructuring the backend to display accurate per-person pricing upfront to reduce cognitive load.
User effort
Information overload
Dev. Effort
Competitor solution
Select to Checkout flow
Product listing tool
Product ranking
Visual explorations.
Final flows.
This user flow maps a system-wide update, addressing every touchpoint across the Headout App and Web ecosystem that interacts with the new pricing logic.
Glossory
City/Collection pages: A city page is a set of collection pages, and experiences that belong to a particular city. Similarly, a collection page, is a set of similar experiences for a particular location/tourist spot. Ex: A collection page for Eiffel tower inside the Paris city page.
Micro-Brand(MB) pages: MB pages are separate branded pages, to rank higher in the SEO. These MB pages are usually made for Cities or collections so that it can catch keywords. Each MB page has its own domain, relating to the name of the location, to make it feel more reliable.
Ex: www.thevaticantickets.com.
Most of Headout's bookings currently come through these MB pages.
Desktop designs.
Major considerations.
We prioritized technical feasibility, ensuring the design strictly adhered to development and listing constraints while fully delivering the intended product value.
API data
API data
The UI was designed to map directly to the current API logic. I utilized existing endpoints for pricing and pax count, ensuring the frontend update could be shipped without demanding any costly backend structural changes.
Internal tools
Internal tools
The solution required an update to the Catalogue team’s listing tool. We added a configurable input section, empowering the team to set the default 'Smart Value' directly when processing vendor submissions.
Product ranking
Product ranking
With 86.4% of our group inventory operating on a hybrid model, we standardized the upfront display to 'per person.' This consistency was critical to prevent changes in our search ranking algorithms, ensuring top-performing products remained visible.
Weaker currencies
Weaker currencies
To guarantee robustness, we validated against the 'worst-case' scenario (Lebanese Pound), confirming the interface accommodates 8-digit figures without layout shifts.
Localization
Localization
The interface was built to be linguistically responsive. Since languages like French often require significantly more horizontal space for discount labels, the design ensured it accounted for these edge cases.
Impact.
As the feature is currently in the engineering pipeline for validation, quantitative results are yet to come. We will evaluate performance based on these key metrics:
Final quantitative results are classified as internal data and will not be released publicly.
Business metrics
Select to Checkout (S2C)
Checkout to Orders (C2O)
Click-Through Rate (CTR)
Retrospective.
What I learned about the "invisible" side of product design: from stress-testing currencies to managing stakeholder needs.
My biggest learning
A redesign shouldn't be measured by the number of pixels changed, but by the value created. Even subtle shifts in the interface can significantly elevate the user experience when they address the core friction points.
