Headout

Headout

Experience booking platform with 49 million+ guests served

Experience booking platform with 49 million+ guests served

Simplifying Headout group booking experience to increase Checkout conversion

Simplifying Headout group booking experience to increase Checkout conversion

Simplifying Headout group booking experience to increase Checkout conversion

The team re-built the group bookings flow to ensure simpler experience across the app, web and Micro-brands.

+42%

Tour selected

+32.8%

Checkout CVR

Team

1 Designer 👋

1 Designer 👋,

1 Marketing Manager

1 Marketing Manager,

1 Product Managers

1 Product Manager,

4 Engineers

4 Engineers

8 weeks (2025-26)

8 weeks (2025-26)

Problem definition

Fitting the group logic into the regular checkout experience

Headout's group pricing had 3 fixed tiers with no flexibility on group size and no per-person breakdown. The checkout experience was forcing users to do mental arithmetic at the exact moment we needed them to commit, a classic friction point in any transactional funnel.

3 types of group pricing logic, currently existing in the Headout experiences


Problem definition

Fitting the group logic into the regular checkout experience

Headout's group pricing had 3 fixed tiers with no flexibility on group size and no per-person breakdown. The checkout experience was forcing users to do mental arithmetic at the exact moment we needed them to commit, a classic friction point in any transactional funnel.

3 types of group pricing logic, currently existing in the Headout experiences


Context

An entire market introduction with Africa

Africa was an emerging priority market for Headout, and group pricing dominated the experience inventory there. With group checkout converting at a fraction of our overall rate, a broken group flow wasn't a niche problem, it was directly blocking growth in a market we'd committed to.

Group checkout converting only 1/4th the overall Headout conversion


Context

An entire market introduction with Africa

Africa was an emerging priority market for Headout, and group pricing dominated the experience inventory there. With group checkout converting at a fraction of our overall rate, a broken group flow wasn't a niche problem, it was directly blocking growth in a market we'd committed to.

Group checkout converting only 1/4th the overall Headout conversion


Research

Why did the users drop-off?

Competitors anchor users on a low per-person price early. Headout led with the group total, triggering sticker shock before users understood the value.

Comparing Headout’s and Competitors’ product card prices for the same experience


Research

Why did the users drop-off?

Competitors anchor users on a low per-person price early. Headout led with the group total, triggering sticker shock before users understood the value.

Comparing Headout’s and Competitors’ product card prices for the same experience


Insights

What the research told us

  1. Users compare experiences with competitors, so it should be a fair comparison between the prices. Hence, showing per-person price was the way to go.

  2. Users should be able to have control over the number of users they are booking for, to reduce confusion.


Insights

What the research told us

  1. Users compare experiences with competitors, so it should be a fair comparison between the prices. Hence, showing per-person price was the way to go.

  2. Users should be able to have control over the number of users they are booking for, to reduce confusion.


Iterations

Exploring solutions within constraints

After exploring several directions with the PM, we landed on the concept that works the best with the constraints and user logic.

Thinking

Showing the math didn't reduce the effort — it just made the effort visible. Users still had to calculate, just with more steps. The problem wasn't transparency, it was that we were asking users to do work at all.

Shows the group price logic upfront

Gives users a better clarity on price break-up

Sticker price still remained high

Still forces mental math on the user


Iterations

Exploring solutions within constraints

After exploring several directions with the PM, we landed on the concept that works the best with the constraints and user logic.

Thinking

Showing the math didn't reduce the effort — it just made the effort visible. Users still had to calculate, just with more steps. The problem wasn't transparency, it was that we were asking users to do work at all.

Shows the group price logic upfront

Gives users a better clarity on price break-up

Sticker price still remained high

Still forces mental math on the user



Thinking

We overcorrected. In trying to eliminate confusion by showing everything upfront, we created a different kind of confusion. More information didn't mean more clarity, it meant more decisions before the real decision.

Builds trust by mirroring the checkout process from the beginning

Includes per-person price accommodating most of the group experiences

Too much information for users to process at once

Hard to maintain these group listing on internal tool



Thinking

We overcorrected. In trying to eliminate confusion by showing everything upfront, we created a different kind of confusion. More information didn't mean more clarity, it meant more decisions before the real decision.

Builds trust by mirroring the checkout process from the beginning

Includes per-person price accommodating most of the group experiences

Too much information for users to process at once

Hard to maintain these group listing on internal tool



Thinking

Users don't compare total prices, they compare per-person prices. That's the only number that needed to be right. The "price varies by group size" tag and a breakdown at checkout would do the rest, so users wouldn't be caught off guard when the total shifted.

Uses a config. number which is set by BDM, which is basically the no. of guests for which the tour is mostly booked for, accounting the price for most users

Shows per-person pricing upfront, helping comparison

Shows a clear break-down of prices in the checkout as well

Requires the catalog team to maintain a config number for each group tour based on the market trends



Thinking

Users don't compare total prices, they compare per-person prices. That's the only number that needed to be right. The "price varies by group size" tag and a breakdown at checkout would do the rest, so users wouldn't be caught off guard when the total shifted.

Uses a config. number which is set by BDM, which is basically the no. of guests for which the tour is mostly booked for, accounting the price for most users

Shows per-person pricing upfront, helping comparison

Shows a clear break-down of prices in the checkout as well

Requires the catalog team to maintain a config number for each group tour based on the market trends


Configurable number was the best solution

Configurable number was the best solution

For V1, we shipped with a standard default rather than a fully configurable number, to validate the core hypothesis before adding operational complexity.

For V1, we shipped with a standard default rather than a fully configurable number, to validate the core hypothesis before adding operational complexity.

Implementation

Translating the concept into flows

Based on the competitive research and the goals we defined for the solution, I iterated on the visual solution of the concept.

Visual concept iterations for the selected logic ideation


Implementation

Translating the concept into flows

Based on the competitive research and the goals we defined for the solution, I iterated on the visual solution of the concept.

Visual concept iterations for the selected logic ideation


Implementation

Internal demo testing & hand-off

After testing it internally with the PMs, Engineers and other Designers as well, who had no context of the solution, the solution was developed and got live on the site.

Thinking

I needed to ensure that the final design accounted for localization in different languages, so that the translations, if longer, shouldn't break the UI, and same with weaker currencies.

Group pricing final concept flows


Implementation

Internal demo testing & hand-off

After testing it internally with the PMs, Engineers and other Designers as well, who had no context of the solution, the solution was developed and got live on the site.

Thinking

I needed to ensure that the final design accounted for localization in different languages, so that the translations, if longer, shouldn't break the UI, and same with weaker currencies.

Group pricing final concept flows


Impact

Performance after launch

What possibly went wrong?

+42%

Tour selected

+32.8%

Checkout CVR

-8.5%

Per-person variant

The user behaviour validated our hypothesis that the competitor comparison primarily led the decisions, and hence we see a significant uplift in the Tour selected.

We also see a slight dip in the per-person booking, but, the significant increase in the group variants brings us to a net positive for the parent level tour.

This dip in the per-person variants suggested that the group audience are being redirected back towards their intended group variants, hence the dip is nothing to worry about.


Before
Redesign
Before
Redesign

Observation

Understanding the user behaviour

2 months into the feature launch, I went through several user session recordings to understand how the users interacted with the feature.

Going through 40 user sessions on Microsoft Clarity to understand user behaviour


Observation

Understanding the user behaviour

2 months into the feature launch, I went through several user session recordings to understand how the users interacted with the feature.

Going through 40 user sessions on Microsoft Clarity to understand user behaviour


Featuring

Featuring

Built a Claude Cowork skill to analyse these user session recordings and document the observations and insights into a google sheet, connecting Mixpanel, Google Chrome & Google Drive MCPs. Github link (duplicate)

Home

Interactions

Not daily UI

Resume

Made it this far?

Made it this far?

Talk to me alreadyy

Talk to me alreadyy

Rahul R Nadkarni

rahulrn.des@gmail.com

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© Rahul R Nadkarni • 2026