In October, 2001 Apple launched the iPod. I was in the room when Steve Jobs pulled the first iPod out of his pocket and gleamed at us. This was a new beginning. From that day on, Apple was able to get on the consumer bandwagon and appeal to individual purchase authority. If a product were very cool and well made and simple and fun, out came the individual's credit card. That has been Apple's mantra and key to success ever since.
Back to the enterprise. When it came to selling Macs of any kind, Apple was, in my impression, carefully treading so that it could dance its own dance. What was at stake was innovation. By that I mean that businesses and government can be plodding -- and demanding all at the same time.
While Microsoft catered to those businesses, Apple knew that it had to move relentlessly forward with technology in order to claim that it makes the very best products. Today, we need only look at the organizations still using Windows XP, even though Microsoft and the U.S. government have pleaded with them to leave that 14-year-old OS behind.
The Influence of Steve Jobs
Very often, the Apple federal and enterprise sales teams would look to the charisma and influence of Jobs to inspire a customer in special executive briefings on the Apple campus. These were customers critical to Apple's business sales.
Sometimes it worked very well, but there were times when Jobs declined to intervene with his influence. It's possible he sensed that a particular technical area was unwise for Apple to pursue, like supercomputing and compute clusters. Plus, there were probably times when he was vey focused on his pet projects, like the iPad and iPhone, and he felt that if his sales team were really, really good, they could close the deal without him.
Finally, as I mentioned above, there's always that enterprise demon -- businesses and government want stability and long-term commitments. That's something Apple couldn't engage in if it were to stay in the business of radical advances in consumer technology.
Apple's approach has generally been to put great products out there while moving forward briskly. If an organization embraces those Apple products, all's well. But if an organization thinks it can obtain concessions from Apple by making high-value purchases, that generally hasn't worked out well. All this explains why Apple pursues the enterprise on its own terms and why there are organizations that embrace Apple and those that consider Apple products and services (or lack thereof) unsatisfactory for their broad enterprise needs.