Why Big Companies Can't Fix Their Customer Service — and Why You Can

I've spent more than twelve years building software inside one of the world's largest corporations. Then I spent an afternoon on hold with one. Both taught me the same thing.

The short version: Calling customer service feels like going to war. I'm going to walk you through the whole battle, because the ending matters: I lost, I left, and the company recorded nothing about why. Then I'll tell you why that keeps happening — not as a customer, but as one of the people responsible for building systems like it. And why your small business can fix in a week what I watched a giant fail to fix in three years.

Part one: the war

Have you ever felt like calling customer service is like going to war?

I do. And the strange part is the war isn't really about money, or a defective product. This one seems designed for a direct assault on your nervous system. Let me walk you through the campaign.

Here I am, getting ready for battle, because my bill went up without any notice — obviously something that failed inside the systems of the company I'm about to call. My objective is simple: reach one human being who will listen, understand the unfairness, and fix it.

I'm already furious before I dial, because I'm being asked to pay more money with no explanation.

→ Nervous system: level 1 damage.

First line of defense. A recording tells me my call is important, then offers me a menu of options engineered to route me anywhere except toward a human — my one objective. So I press "0". That's my trick. Sometimes it works. Other times you press it, and press it, and burn four minutes proving to a machine that you are not going away, until finally a flicker of hope: you might be routed to a real person.

→ Nervous system: level 2 damage.

Second line of defense. This one might not count as a defense for other people, but for me it absolutely does. The looping message. The music. The worst music you have ever heard in your life. You tell yourself it won't be more than a couple of minutes — and then you glance down at your phone and discover you have been holding for thirty-one minutes.

→ Nervous system: level 3 damage.

Third line of defense. Someone answers. A human. Yay! You explain your story using the most compelling words you own, hoping this is finally the moment — only to discover that the person you've reached is the least empowered employee in the entire company and has no authority whatsoever to fix your issue. So you ask for a manager.

→ Nervous system: level 4 damage.

Fourth line of defense. Looping music again? If you're lucky there's no music, so let's file that under the second line of defense you've already survived. A manager picks up. A little bit of hope! — which vanishes the instant you realise you have to explain yourself all over again, from the beginning, because nothing you said travelled with the call.

→ Nervous system: level 5 damage.

Fifth line of defense. Because these systems are designed in a fundamentally non-human way, customer service teams handle thousands of identical calls a day. So guess what they're trained to deliver? Not a fix. A response — one that has been through legal review, commits to nothing, and makes the company liable for nothing. Most of the time your issue is not solved, and these days they don't even flinch when you threaten to take your business to a competitor.

→ Nervous system: level 6 damage. I am seriously injured.

But I'm persistent. I can't lose the war that easily. I notice the company has a chat option, so I start typing. I explain my problem in plain English, and I'm met with automated bot responses that cannot parse it — options that are, if I'm being generous, trying to guide me toward the right agent. After a few minutes of this I finally reach a human.

And after a few more exchanges I get them to actually look at my account. Hope again? Not so fast. The agent is reading from the same knowledge base the phone agents were trained on, so I start hearing the same sentences all over again.

At this point, why bother threatening to leave? My nervous system is already in a coma. This war is no longer worth fighting.

My final decision: find a competitor, and hope this never happens again.

Part two: the silence

It's funny, in a way, because almost everyone has lived some version of this. But if you own a business and your customer service has quietly turned into something similar, that comedy has a price, and you are paying it every single day without seeing the invoice.

Here is what that company recorded about the worst afternoon I had that month:

Nothing.

I never escalated past a manager. I never filed a complaint. I never left a review. There is no ticket anywhere saying customer left over a billing change and thirty-one minutes of hold music. From the inside, I'm not a lost customer with a reason. I'm a rounding error in next quarter's churn number.

Most people don't complain. They leave, and they take the explanation with them.

The loud customer is a gift — at least you know. It's the quiet ones that cost you, because you're paying to acquire replacements for people who left over something you could have fixed for free, and nothing in your reporting will ever tell you that's what happened.

Part three: the part most people never get to see

So is the fix to swap the bot for AI?

Everyone writing about this lands on the same conclusion: the systems are badly designed and don't talk to each other. That's true. It's also the least useful sentence in the conversation, because it implies somebody was careless.

Nobody was careless. I know, because for twelve years I have been one of the people responsible.

I'm a digital product manager. Inside that corporation I've owned internal platforms — the largest a Salesforce environment serving around 300 users. That's not the call centre of a telecom giant, and I won't pretend it was. But the mechanics are identical at every large company, and I sat in the rooms where ideas like "should the billing system tell the customer before the price changes" get decided.

Here's what happens to that idea. It is not rejected. It is ranked. It joins a list next to a compliance deadline carrying a fine, a platform migration that's already late, and a revenue feature with an executive's name attached.

Proactive customer notification has no deadline, no fine, and no executive sponsor. It is genuinely valuable, and it loses — every quarter — to things that are merely urgent.

And it loses for a second reason that's harder to fix: nobody owns the afternoon I just described. Billing owns billing. Support owns support. The website belongs to someone else. Every one of those teams hit their targets that quarter. My war happened in the space between them, and at a large company nobody's job description covers the space between.

I never sat in a meeting about billing notifications specifically. But I have been on the losing side of that exact calculation more than once.

In 2016 I argued that most of our customer service problems could be solved by moving to a CRM that gave us a single view of the customer — one place where anybody speaking to a person could see everything about them. The idea was turned away. Then it was turned away again. It was finally approved, partially, in 2020.

Four years. And not because anyone disagreed — I never once heard someone argue that a single view of the customer was a bad idea. It simply never had a deadline, and every year, something else did.

Now read back the afternoon I described at the top of this article. The agent who could see my bill but not the reason for it. The manager I had to tell the entire story to a second time, because nothing travelled with the call. That is exactly what a single view of the customer prevents. Somewhere inside that company, I'd bet someone raised it in 2016 too, and was told it wasn't this year's priority.

This is why adding AI to a broken process doesn't repair it — it makes it fail faster, at higher volume, and more politely. You'll have automated the wall.

Because my problem didn't start at the phone menu. It started thirty days earlier, in a system that knew with certainty that a specific price was changing for a specific customer, and had no way to tell me like a person would. That system didn't talk to billing, which didn't talk to support, which is why the agent I finally reached could see my bill but not the reason for it.

By the time I reached level 1 damage, the failure had already happened. Everything after that was cleanup.

Part four: the advantage that just changed hands

For most of my career, the giants won anyway. Not because they were smarter — I've been on the inside, they are not smarter — but because they could afford to paper over the structure. They could buy the integration platform, staff the team, and run the three-year programme to connect two systems. A ten-person business could not. That was the entire game.

Look closely at what that means: their advantage was never talent. It was that connecting systems used to be expensive.

That is the specific thing that stopped being true.

The work that used to require a programme budget — watching for the moments that turn a customer into a caller, and reaching out before they pick up the phone — is now something a small business can put a system on. And here's the part that still surprises me: a ten-person company can now do this better than the corporation can, and faster. Not because it has better tools. Because it doesn't have the structure that kills the idea.

You have no prioritisation committee. No competing roadmap. No four teams each owning one slice of your customer. You can decide on Monday that nobody will ever be surprised by a price change again, and have it running by Friday. I have watched that exact decision take three years and never ship.

The giants were never smarter. They could just afford more. They can't afford more anymore — because it no longer costs more.

Part five: your customers are on that ladder right now

Here's the uncomfortable thought to sit with. Somebody is at level 2 with your business today. You will never meet them at level 6, because they won't call to tell you they've reached it. They'll just stop.

The moments that start the climb are almost always knowable in advance. A price is changing. A delivery will be late. A renewal hits Friday. A regular hasn't booked in four months. Every one of those is already sitting in a system you pay for, and every one becomes a furious phone call if nobody says anything first.

Before you buy any customer service software, spend one afternoon on this:

1. Call your own business from a number nobody recognises. Time it. Count the steps between a customer and a person who can actually decide something.
2. Email your general inbox as a confused customer with a real problem. See how long it takes, and what comes back.
3. List your last ten complaints. Next to each, write the moment it became inevitable — not when the customer contacted you, but when the thing went wrong. Count how many were knowable in advance.
4. Find the customers who stopped. Not the complainers — the quiet ones who stopped booking, ordering, or renewing. Call three and ask what happened. It's an uncomfortable hour and the most useful one you'll have this quarter.

That afternoon tells you whether you have a support problem or a systems problem. They need completely different fixes, and almost everyone buys the wrong one. (We answer the most common versions of that question on our FAQ.)

Where we come in

This is why Cherish AI doesn't lead with a product.

We start by finding where your systems stop talking to each other, and which of your customers are quietly climbing that ladder right now. Sometimes the answer involves AI. Often it's a process change and a connection between two tools you already pay for — which is why our services start with an assessment rather than a product.

I've spent my career watching good ideas lose to structure. I started Cherish AI because small businesses don't have that structure — and for the first time, the technology doesn't demand it.

The goal was never to make your business sound smarter to a furious customer. It's to make sure fewer of them ever had a reason to go to war.