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5 Times We’ve Pissed Off Our Customers And What It Taught Us

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Every startup will upset some of its customers as it learns and grows.
Here’s how we dealt with it…

In a lot of ways, being a startup is like being a kid.

You’re not like the “adult” companies that have been successful and running well for years.

You don’t have it all figured out.

You still have everything to learn, and along the way, you’ll break stuff, do things wrong and make the people who support you angry.

What sucks most is that because none of us are actually kids, we have a lifetime of developing empathy and emotional intelligence, so we deeply understand the consequences of pissing off our customers.

That’s what makes it so terrifying.

But it’s a part of growing up, so to speak. And every startup will go through it. The best you can hope for is that each time it happens, it’s a learning experience and you apply what you learned to making your business better for your customers, and ensuring that whatever happened doesn’t happen again.

In our history, I can think of five times we’ve really upset customers. Here’s what happened, what we did about it, and the lessons we’ve learned that have helped us get through it all.

1) Changing Our Prices.

This is one of the scariest things we’ve ever done.

We had quite a bit of internal conflict over whether we should change our prices at all, or whether it would annoy our customers so much — and look so unbelievably amateur — that they’d all walk out the door.

When we first launched to the public three years ago, we had a freemium pricing model with three tiers:

Our conversions were pretty low (just over 1%), and we thought that maybe we weren’t giving customers enough options (I’ve since learned that this is almost never a good assumption).

I wanted to add different pricing options to “reach” more people. But we were all scared of what might happen. It took us weeks — painful, business-killing ages in startup time — to finally work up the courage to do it.

Still, we went through with it and launched a pay-as-you-go model:

The result?

Not only was this offer a total flop, but we made a lot of people confused and angry.

It turned out that pay-as-you-go scared a lot of customers. They didn’t want to have to think about how much they’d be spending that month. Business budgets don’t work that way; customers want to allot a specific amount for each expenditure, and our scheme didn’t really encourage (or allow for) that.

So not only did we piss off our customers and prospects by changing our prospects, but it was clear that we’d have to do it again.

Twice more, in fact, until we got to the pricing we have today: two simple tiers (one free), and a single straightforward price.

And while some customers were still upset at the simple fact that we changed pricing at all, we gave them the option to be grandfathered in at whichever plan they wanted. This satisfied most, and this pricing model continues to work well for us today.

Takeaway: Pricing is a sensitive issue for customers, but they don’t necessarily want more options. They just want a plan that works perfectly for them, and adding options doesn’t always lead to that. In any case, be very careful testing pricing, and be sensitive to the fact that you’ll likely need to make plenty of concessions to existing customers to treat them fairly.

2) Changing Free Trial Length.

We always knew that we’d be testing different free trial lengths to figure out what worked best.

When we made our product demo video, we even had the voiceover artist record different lines when we called on customers to “sign up for your X-day free trial now.”

But that didn’t make customers who got shorter trials any less angry.

We’ve tested 7, 14, 30 and 60-day free trials. Today, everyone gets a 30-day trial (and we’ve got a post coming up about why that’s worked best for us), but how would you feel if you got a 7-day trial, and later learned that we offered a 60-day free trial?

I’d feel pretty shitty about it, considering it would mean that I paid for nearly an extra two months more than the 7-day trial customer.

We wanted to be fair to our customers, but we couldn’t simply give everyone the 60-day trial because it would screw up our testing. So if a customer noticed and raised an issue, we wouldn’t hesitate to extend their free trial.

We no longer have to do this as our free trial hasn’t changed in months, but it was a painful learning experience in doing what’s right for the business (and customers) in the long-term at the cost of pissing off a few customers in the short-term.

Takeaway: Testing is an important part of any business, but it invariably means that some customers will get a “worse” deal. If they ask, don’t hesitate to make those customers whole.

3) Killing One of Our Biggest Features.

When we first launched Groove, we had two “core” products: our help desk app, and our live chat software.

We had too many competing messages, and it confused visitors enough to keep our conversions quite low:

Over time, it became clear that the two-product route was a mistake. Our engineering team was stretched too thin supporting both, and neither app got the attention that an early-stage product so desperately needs.

Instead of a single app that we were proud of, we had two that were under-developed.

So a year ago, we made the tough call to kill live chat to save our business.

While some customers were supportive…

Others didn’t agree with our decision:

Though importantly, we were probably saved by the transparency and honesty we took with the decision, rather than simply labeling the change as an “enhancement” as I’ve seen many companies do:

Takeaway: If you’re going to make a drastic change to your product, be honest about why you’re doing it. Nobody buys the “enhancement” excuse anymore, but people do appreciate you respecting their intelligence and wanting to focus on making the best product possible for them.

4) Sharing Feature Release Dates.

In the past, when a customer was having issued that would be solved by an upcoming feature release or update, I’d happily respond with the good news:

As any experienced developer or product manager knows, these promises can be very dangerous.

Between development and thorough testing (which can sometimes uncover serious issues), planned release dates don’t always get hit, and I personally pissed off more than a few customers by making promises that we couldn’t keep.

A tough lesson to learn; in the early days of a startup, there’s often so much bad news that we grasp at straws to deliver good news whenever we can. But that can — and has — come back to bite us, and we no longer share feature release dates until features are tested and ready to deploy.

Takeaway: We don’t hit our milestones 100% of the time, and you probably don’t either. It’s better to be honest about not being able to perfectly predict the future, than make promises that you may be forced to break.

5) A 15-Hour Outage.

This one still hurts to relive.

Early last year, a server outage brought Groove down for more than 15 hours.

It was, to put it bluntly, catastrophic.

It cost us a lot of goodwill, trust and customers:

It was easily the worst single day in the history of our company, and my worst day ever as a founder.

That day, we committed to stepping back and re-focusing on the core infrastructure of Groove. By the end of the week, our development team had put a plan together to make that happen, and we did nothing for the next several weeks until that project was completed. We’ve had 99.9% uptime since then.

Takeaway: Building features and growing your business is great, but don’t ignore the stability of your technology. While the outage wasn’t cause by Groove, it could have been prevented by Groove with the proper precautions in place. That’s a lesson we’ll never forget.

Investing In Customer Relationships Matters… A Lot

While the outage made many customers angry, it could have been a lot worse. We were extraordinarily lucky to have gotten so much support and understanding:

To me, this was a validation of the massive amount of time and energy our whole team spends on building relationships with our customers.

It’s why I try to talk to every customer.

It’s why we’re always asking our customers how they’re doing with Groove.

And it’s why I spend 20+ hours per week doing support.

Your product matters. Your customer relationships matter more. When your product fails, your relationships will save the business.

How To Apply This To Your Business

It doesn’t matter how good your product is, you will make your customers angry at some point. It’s not an if, it’s a when.

Focus on building great relationships with your customers, so that they’ll be understanding and forgiving when you need it most.

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From “aha” to “oh shit”, we’re sharing everything on our journey to $10M in annual revenue. We’re learning a lot and so will you.

About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

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