How to Retain Customers, When AI is Pushing Them to Competitors

You don’t just lose customers to price—you lose them to hesitation.

Search engines and AI tools deliver answers instantly, without needing a click.

Fewer clicks mean fewer chances to bring in new customers. And the ones who do visit your site are likely to be higher-intention.

This is a major headwind for many businesses.

Conversion rates and retention are more critical than ever.

In the first chapter we looked at how price perception shapes decision-making.

Today, we’re diving into something even more important: building retention and loyalty over multiple sessions.

Or in this instance, how most of these platforms accidentally drive customers away.

Most of the time, push notifications have become the "we don't know what to do, so let's just remind them we exist" strategy.

Price alerts fall into a different category though, because they're 📮 User-Initiated Triggers.

It's communication with permission, and it serves a clear purpose.

You won't be surprised then, that they mostly look like this:

They're purely transactional. Any incentive to act is internally-driven.

i.e., "oh, the price is down, I should buy it".

It requires the recipient to connect the dots between information and action.

Often alerts would be obviously wrong.

My assumption that they'd alert me to every price movement was naive.

Over the same two-week period, this is how often each provider notified me of a change.

(And, as a reminder, they're all basically tracking the same airlines).

In other words: on totally different days.

If they really were tracking prices by the minute, you'd expect the notifications to be clustered around specific events, which they're not.

I suspect that this is down to a few boring technical reasons (rather than being intentionally misleading):

• The APIs connecting providers to airlines are probably inconsistent and often not in "real time". 
• The providers need to set their own crawl frequency, and there are likely higher costs associated.
• Tracking thousands of flight combinations, including all possible layovers, for every route, is probably much harder than I'm giving it credit for.

So my question is this: if price alerts don't always work (which they don't), how can you make them more valuable?

Well, take a look at Hopper:

Notice that it's more or less the same notification, but they've contextualised what you're seeing.

It's a trojan horse of an alert: you think it's about the price, but it's really about giving you a nudge to take an action.

You may have noticed that Kayak sent me no price alerts during that period.

But that doesn't mean I didn't get notifications. I got four of them.

It's just that they were the same two, twice.

It was an almost identical email, where 13/14 of the times it said prices were steady, whilst telling me a slightly different price.

I get it, there's some tolerance here about what a "price change" is. 

But you start to notice that the prices are changing, while being told that they're not.

They then immediately show you "today's top deals", which include flights that clearly aren't a deal.

Kayak are training people to ignore their emails.

Let's end on a lighter note.

In the study we looked at Hopper, and the subtle difference between "Finish my booking" and a standard "view prices" call to action.

In other words: how Hopper creates an action-oriented link, which reinforces the effort that the user has already exerted to that point.

That demonstrates an attention to detail.

But let's look at an example where the product builders were asleep at the wheel.

If your Skyscanner results are more than 30 minutes old (i.e., if you return to the app later), then you'll see this:

At first, it might seem okay. 

Then you start to wonder what the difference between "Refresh" and "New Search" is.

Here's the thing: you could remove any confusion in about 10 seconds, by renaming that second action "go home" (which is what it does).

Instead it's basically this meme.

In the third chapter of this study, we dive into the world of deceptive checkouts.

When you factor in the cost of selecting a seat, adding bags and some flexibility in your fare, it can 3/4x the price.

This is how you end up overpaying.