Enterprise Software CEOs Need a Dose of “Undercover Boss”

Connecting with the Disrupted Customer

What if enterprise software company CEOs were asked to do what other CEOs are doing on the TV show "Undercover Boss": to do the heavy lifting that their employees are doing every day? (It always makes me smile when I imagine Larry Ellison trying to write SQL.)

I think we'd find that there are very few software CEOs who appreciate what’s involved in developing or deploying their technology into the hands of customers. (Jim Goodnight at SAS may be a notable exception).

Most software CEOs can probably do what the average enterprise software salespeople do:  sit in meetings, make phone calls, and invent new PowerPoint charts.  But how many could actually put their hands on a keyboard and write code? Or even just configure their company’s products in order to create value for their end-users?  Although watching people – even great engineers – write code and run build-scripts isn’t quite the same as watching some executive load a garbage truck with dirty diapers during primetime.  

Obviously, I am having some fun here: programming is probably not required for running a multi-million-dollar or billion-dollar software company. But I'd go as far as to say that it's highly desirable for the CEO of a software company to understand the engineering of her/his company's technology.  Furthermore, knowing your customers (mostly engineers) and their needs is absolutely a requirement.  And, in general, it’s often incredible to me how disconnected many technology company executives are from what their products actually do for their customers’ end-users.

With the rapid maturation of the enterprise software industry over the past 10 to 15 years, the “nobody ever got fired for buying IBM” excuse is going away.  When buying enterprise software, customers today have many options and often radically reduced switching costs. They also have the ongoing pressure to improve efficiency of both capital and operating costs.

Meanwhile, corporate end-users are asking themselves and their managements: “Why can’t the systems that I use at work be as easy to use, simple and productive as the systems I use at home?”

Good question.  If your company has decided to use Google Enterprise Apps, you have an advantage. The capabilities you have from Google will improve at the pace that technology moves on the consumer Internet – not at the pace that your internal IT organization moves.  Many users who are frustrated with their captive IT organizations just pull out their AMEX cards and pay for cloud-based services that do the job without involving requiring a call to anyone in IT.  This is how Salesforce.com got its start and how systems such as Expensify today are replacing traditional enterprise expense management tools.  (Expensify has the best tag line in the world, in my opinion: “Expense reports that don’t suck!”)

If you work for a traditional enterprise software company, the consumerization of IT should be a huge wake-up call. If you are the CEO of one of those companies, I'd suggest embracing a model other than "milk my customers for maintenance revenue."

Even if you don’t expect a software company CEO to write code on national TV, it’s a good idea for her/him to get together with end-users who are actually using the software (or, more worrisome, not using it).  Then, he/she will have direct information on how good (or how bad) the software actually is and can make the decisions necessary to fix it quickly if necessary.  Start-up CEOs have the advantage of being closer to their customers, for both constructive feedback and complaints. A little start-up thinking could go a long way for most large enterprise software companies.

But I’d still like to to see the CEO of a large enterprise software company write some code ;)