Headout

Experience booking platform with 49 million+ guests served

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.

~46%

Increase in the Checkout conversion so far (goals not met)

Increase in the Checkout conversion so far

(goals not met)

Team

1 Designer 👋

1 Designer 👋,

1 Marketing Manager

1 Marketing Manager,

1 Product Managers

1 Product Manager,

4 Engineers

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

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

Context

Why now?

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

Why now?

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

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.
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

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.
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

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

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

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

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

Shipping it

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

Shipping it

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

~46%

Increase in checkout conversion so far

Going through the funnel, it might look like there was a 46% increase in the conversion of the funnel, but it still didn’t meet the goals set for these tours.

New group checkout conversions - 2x more compared to the prev. group checkout, but still falls short on the overall

Impact

Performance after launch

~46%

Increase in checkout conversion so far

Going through the funnel, it might look like there was a 46% increase in the conversion of the funnel, but it still didn’t meet the goals set for these tours.

New group checkout conversions - 2x more compared to the prev. group checkout, but still falls short on the overall

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

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)

Inference

What possibly went wrong?

It was known that 86% of our group experiences came as a combination of per-person and per-group tours. I realized, even though the group funnels had a severe drop in the select stage, the overall conversion of the experience was on par with Headout.

This meant that the users were just not choosing to go with the group variants because they didn’t find it relevant to them.
From the recordings, it was implied that the users seeing a different price total at the checkout, in place of what they saw up until selection led to drop-offs.

Thinking

This made me wonder, how are the competitors doing the same thing and still working? What is it that we did differently that didn’t make sense to the users? Turns out, it could mostly be because the competitors’ checkout is on the same page - hence easier comparison between what was initially shown and what is finally the price.

Select and checkout conversions comparison - actual numbers are confidential hence hidden

Inference

What possibly went wrong?

This meant that the users were just not choosing to go with the group variants because they didn’t find it relevant to them.
From the recordings, it was implied that the users seeing a different price total at the checkout, in place of what they saw up until selection led to drop-offs.

Thinking

Select and checkout conversions comparison - actual numbers are confidential hence hidden

Actionables

Giving it another shot.

Two things stood out from the recordings as the primary reasons for drop-offs:

During checkout, the users couldn’t understand the price jump even with a breakdown visible, which is the primary reason for drop-offs.
At the select stage, most users didn't engage with the group variant at all, suggesting it didn't feel relevant to them.

The next iteration needs to make the group variant feel worth clicking, and the price feel expected, not surprising, at checkout.

Thinking

The "price varies by group size" tag likely read as a warning, not context, causing users to skip the group variant entirely. And since these are mostly private or VIP tours, the per-person price was always going to look higher against standard listings.

Actionables

Giving it another shot.

Two things stood out from the recordings as the primary reasons for drop-offs:

During checkout, the users couldn’t understand the price jump even with a breakdown visible, which is the primary reason for drop-offs.
At the select stage, most users didn't engage with the group variant at all, suggesting it didn't feel relevant to them.

The next iteration needs to make the group variant feel worth clicking, and the price feel expected, not surprising, at checkout.

Thinking

Home

Interactions

Not daily UI

Resume

Made it this far?

Talk to me alreadyy

Rahul R Nadkarni

rahulrn.des@gmail.com

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