Smile Software Launch Tries to Turn That Frown Upside Down

Last week must have been a terrible week for Smile Software and their software launch, one I never want to experience. In case you missed it, you can do a bit of searching around the web to see the result of a new and not well-planned one. The announcement was for a new version of TextExpander for Mac (v6) and iOS (4) along with a new backend service for syncing snippets.

We’ve updated our pricing model to match our new service. Instead of license purchases and upgrades on an irregular schedule, we’ve switched to a subscription model where you pay monthly or annually for your TextExpander service. This lines up with the regular costs to provide an online service. It also frees you as customers and us as developers from the “upgrade treadmill.” We can offer our apps free of charge. We can deliver incremental improvements as they’re ready rather than wait and package them all into a new “big” upgrade release. We’re really excited about what this change will allow us to offer our customers, and we hope you are too.

The problem being the new backend with monthly subscription, replacing the previous upgrade pricing. The result is a yearly fee that could be quite a bit higher than Smile Software customers were accustomed to. They welcomed feedback, and they got it.

I wasn’t happy and tweeted about it, as did many others. It appeared existing customers would be shut out from support of previous versions; either pay up, stick with unsupported software or find an alternative.

It would have been appreciated if existing customers were notified of the planned changes prior to reading a MacStories post. It seems I receive an email from Smile almost weekly, but this important news never hit my inbox.

Initial Reaction Triage

I would liked to have been a witness in the Smile headquarters as the immediate feedback started pouring in. I can only imagine there were some surprised faces. Smile did take the feedback and announce some revisions to their plans, a bit reactionary but an attempt just the same.

With regards to pricing:

Discounted upgrade pricing is available to customers of any past version of TextExpander. The details are found here. To take advantage of upgrade pricing, sign in to, click your avatar at the upper right, choose My Account > Billing, and enter any prior serial number or license code. If you have any trouble, please contact support and we’ll help get it sorted.

For those happy TextExpander 5 customers:

For those who prefer to stay with TextExpander 5 for now, we intend to support it on El Capitan and the next major upgrade of OS X (…Humboldt? 😀). Beyond that, neither we nor anyone else know what to expect of Apple or OS X. We also hope to encourage you to join the new TextExpander at some point in the future.

It didn’t seem to go far enough:

Your feedback is important and does matter. Expect an update on The State Of TextExpander (based on your comments) very soon.
— TextExpander (@TextExpander)
April 11, 2016

Loyal customers are passionate and vocal when they feel they weren’t treated fairly. In a very short time Smile realized they had a passionate customer base.

Doing the Right Thing

One week later and I’m sure after some thoughtful conversations at Smile, I received an email with additional refined plan for the new TextExpander launch.

Our changes to TextExpander last week made a number of you unhappy, and many of you shared your passion for the product with us. We are equally passionate about TextExpander and have made these changes so that we can expand the customer base and continue to enhance the product for all users.
To some of you it may seem we don’t care about our individual customers any more and only care about business use. We care about both, and in the changing software world a single focus is not a viable long term strategy for TextExpander. We did not make these changes easily or lightly, but for the long term life of the product so we can all enjoy it and engage with it for many years to come.
Change is difficult, and we didn’t get some things right at the start. Our pricing for Life Hackers was too high. Our upgrade pricing was too high and did not extend long enough. We didn’t offer an option for users who cannot use third party cloud services or cannot purchase subscription software.
We’re listening to your feedback, and are making adjustments, effective immediately.
Standalone TextExpander:
TextExpander 5 for Mac and TextExpander 3 + Custom Keyboard, the most recent standalone releases of TextExpander, will continue to be supported, and available for sale.
We understand this is important if you need: — private-network snippet storage — sync via Dropbox or iCloud Drive
New Pricing:
You, and other current TextExpander customers, receive a 50% lifetime discount on the new TextExpander. This brings the yearly cost of the Life Hacker plan to $20, which is comparable to previous upgrade costs ($19.95). If you aren’t sure about the new sharing features, or just want to test the waters beyond the demo period, you can pay $2.08 monthly to experience the new features before committing to the discounted $20 annual plan. The cost for new purchasers of the Life Hacker plan is similarly reduced to $40 per year.
If you’ve already purchased an annual upgrade plan, we’ll apply two months of credit to make up the difference. Please give us a few days for this to be reflected in your account.
From our team to you, thank you for being part of the conversation that makes the community around TextExpander what it is, and helping us continue to develop and improve TextExpander.It seems Smile could have avoided the unnecessary criticism with a better planned launch. Of course, it easy to tell someone else what they should have done. I’ve handled or been part of a few software product launches myself and try to do things a bit different.

This email probably contained most of what should have been sent to customer before the MacStories post was published, days before the launch.

My Software Launch Checklist

This should be common sense, but maybe not:

  • Communicate well from the beginning — Once you have a plan for a new release, make sure everyone is on the same page. This doesn’t just include those people on your team and in your company but, more importantly, your customers. Make them aware early, before the press and social media gets ahold of it. Hopefully your customers can give you feedback before the larger world has a chance to tear you apart.
  • Step into your customer’s shoes — Given the plan, how do you think your customers will react? Maybe there’s nothing to react to, but maybe there is. In the case of Smile, there was a lot to react to. Current customers are why you are where you are now and they should be treated as such. In the case of a pricing change, loyal customers should know their appreciated, reward them for their loyalty.
  • Be clear why the update is better — Again, this is about the customer and not about your company. You may be changing things to improve your aspects of your business such as cashflow or support, but give current customers the reasons this will be better for them. “We screwed up our pricing and need more money” is not a very good reason, unless of course you want to reset your customer base and start over.
  • Provide a special offer, if applicable — If pricing or service terms are changing then reward the loyal customer. Give a discount or even grandfather existing users. They will appreciate you are thinking of them and in-turn know you appreciate them.

My approach isn’t magic. It isn’t revolutionary but reflects what I’ve learned over the years. Planning and communication trump bad surprises every time.

I still haven’t decided if I will upgrade to the new TextExpander. I’m not clear on why I should; features aren’t better than I have now but the pricing is fair. The story from Smile isn’t complete, they are still busy fixing things.

Originally published at on April 13, 2016.

Like what you read? Give Rob Bazinet a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.