software_insideBecoming a Web business isn’t as easy as it looks. Take the weight loss giant Jenny Craig. I’m on my second day of the program in an effort to lose baby weight. I picked Jenny Craig, because I know people who’ve had success on it, and I love the idea of someone else planning meals for me. Part of the reason I can’t eat more healthy is my busy schedule.

Going into the strip mall weight loss centers was a non-starter — again, given my schedule, the fact that there’s not one near my house, and that it arbitrarily closes early on certain days. Fortunately we live in an era where software is eating the world.

To that point, Jenny Craig offers a “Jenny at Home program” that should be an example of this. It’s certainly not a tech company, but it’s a company that only continues to thrive and grow if it embraces software and the Web. Just look at our earlier story about Stronger for one of many examples of a company that will take older weight loss companies like Jenny Craig out if they don’t modernize and become more flexible.

It’s not as simple as just having a Web interface — there are also supply chain issues with ordering and mailing food, since customers aren’t picking it up in stores. But that’s all totally solvable by software. And if more customers become Jenny at Home customers, well, that means it can expand without all that costly brick and mortar.

A win for everyone! Yay, software!

It started out so well. My nanny is doing the program with me, and we called to give a very friendly woman in a call center all of our info. She was a mother of six who’d used the program and had a lot of insight. She was most definitely not reading from a script. It took a little while to go through all of our information — filling out a form on the Web for some of it would have been a hell of a lot more streamlined. But it was a page out of the Zappos-customer-service playbook, bringing the same warm service we’d get in a Jenny Craig center into our living room. So well done on that. There’s also a weekly coach who calls you to check in and answer questions.

So they’ve done a decent job when it comes to the human side of Jenny at Home. But so far everything that software has touched has gone horribly wrong. We are only two days in, and so far our order has been scheduled to go to the wrong address with the wrong amount of food. There were several missing parts of it, and I was put on the wrong plan, because the system deleted the little fact that I was nursing, and hence burning an extra 600 calories a day.

At each turn, we’ve had to call into a call center, spend several extra hours on the phone in all, and had to have someone manually fix each of these things, re-entering them into what appears to be a hopelessly buggy software system, and push out more changes.

The people on the phone are always nice and apologetic. They explain that they just have some issues with “the system.” There’s a lot of talk about “the system.” They’re all very cheery, but you can tell they all really hate “the system.” “The system” doesn’t enable them to do their jobs. “The system” actually inhibits them from doing their jobs. From what I can tell, two days in the manpower servicing our account has been double what it should have been, and the problem seems to be Jenny Craig’s “system.” That, or it’s company-wide human error, which is ultimately also a software problem.

Really? In 2013 we’re not yet to a point where software doesn’t solve more problems than it creates?

I’ve been pretty patient so far because the women we keep talking to on the phone are so nice, and I feel sorry for these horrible tools that have been thrust on them. Tools that I have no doubt are leading less accomodating customers to cancel or demand refunds.

This is why startups get footholds in markets like these, and this is why old industries are resistant to change. It should be so easy for Jenny Craig. They have the brand. They have positive word of mouth. They have user trust. They have a proven system for losing weight. They have deep pockets. All they needed was software that worked to extend their strip-mall-weightloss franchise to the world at large. Unlike industries like journalism and music that are moving online, it doesn’t even have a monetization problem. We’re paying the same prices for the service that we’d pay in the store.

The problem with cases like these — and we’ve all experienced plenty of them; I don’t mean to pick on Jenny — is that every company and industry needs software to stay competitive at this point, and most of it needs to be custom-built. As the bitching about the tech industry’s war for talent makes clear, good programmers are a finite resource.

Even if companies like Asana and Yammer and Box can make everyday workplace software less shitty, there is still a much larger universe of custom software with functionality and user interfaces that’s still stuck in the 1990s. And I don’t see how they’re all climbing into 2013 anytime soon.

Sure software can make all of these companies run better. But only if it’s good software. We all know software is eating the world, but sometimes when software tries to automate a non-tech industry, it gets indigestion.

[Illustration by Hallie Bateman]