Apple, Steve Jobs and Salesmanship

Apple co-founder Steve Jobs

It was, as I recall, November of 2001 and the customary congregation of the Apple sales team was underway. The kickoff meeting was in what was called Town Hall on the Infinite Loop campus.

Steve Jobs

Steve Jobs and Phil Schiller presided, and this meeting was a combination of kick-off meeting and Q&A with Steve and Phil. There were lots of questions for Steve, but the one I recall vividly was from Mike, one of our federal sales System Engineers. (System Engineers provide technical support to the sales executives and their customers.) The Q&A went roughly like this:

Mike: Mac OS X is shipping now. When are we going to get some sales support with TV advertising?

Steve: That’s the job of the sales team. Or. I could just fire you all and spend the money saved on TV ads.

A hushed silence pervaded the room. We knew he wasn’t serious. But…. When Steve got a bee in his bonnet, there was no telling the outcome.

The point was that Steve was the consumate salesman. He could sell sea water to a drowning sailor in the ocean. He expected the same performance from each of us execs. Apple had a superior product in the Macs and Mac OS X, as it was called then. Go sell it!

However, that wasn’t enough.


Most of Apple’s target enterprise and federal customers at the time were deeply committed to Microsoft. Years and years of checking the customer boxes of needs were in place. Meanwhile, in the late 1990s, Apple was floundering with a toy OS, Mac OS 7,8,9. IT managers had, in place, a Microsoft ecosystem which, while far from perfect, met corporate needs and kept them important and employed.

Even as Windows XP was a total disaster, riddled with malware vulnerabilities. The devil they knew….

Apple introduced Quick Look in Mac OS X Leopard
Mac OS X was vastly superior to Windows XP. No matter.

Adopting a superior product, the Mac, was not realistic. It requires a first order UNIX guru to set up a UNIX network of directory services, email, NFS file sharing and collaboration. And grey beards are weird and difficult to manage. Microsoft had a skilled sales and support team to depend on.

That’s why Macs/Mac OS X found initial favor with scientists and researchers at major national laboratories — hotbeds of UNIX culture. But the sales were small potatoes, and Macs had about 2% market share.

As an aside, it wasn’t until the “Get a Mac” TV ad campaign in 2006 and the Phone in 2007 that Apple solved the enterprise puzzle.

Turning the Tables

Apple has learned a lot about “lock-in.” That’s when the customer is completely ensnared in and committed to a technical ecosystem. Even if a competing product is superior, it would require too much time and expense to be a Switcher.

Like the Microsoftians of the 1990s, today’s Apple customers suffer their share of travails. Error prone, awkward keyboards on MacBook Pros, lost email in macOS Catalina, spontaneous macOS logouts, sneaky iOS apps, awkward errors in Maps app, and so on.

We muddle through. Even if there were a brilliant Windows 11/Office 2022 sales team, some day in the future, how could we bring ourselves to switch to something that might be demonstrably better? (Probably not ::cough::) Ponder how we, today, are just as locked in as those Windows IT managers of old.

It’s ironic. Customers get set in their ways. They experience a technical Stockholm Syndrome. Salesmanship can only do so much in that kind of environment. Real change comes from bolt-from-the-blue brilliance — like what the iPhone did for Apple.

That’s why tech journalists harp on Apple to be innovative. The next iPhone-like disruption is out there. The question is, as always, how will Apple fare? And how locked in are we really?

One thought on “Apple, Steve Jobs and Salesmanship

  • I do not like the new 16″ Keyboard. Still no Key Depth.
    I do not like the Touch Bar and enlarged trackpad, both are error prone and unreliable with trackpad causing more false positives.
    Nothing in the past few macOS release had any features I use or like. Except performance and bugs are constantly on the downside.
    I was ready to spend $2999 on a new Mac Pro except Apple completely priced me out with their new Mac Pro pricing.
    No New iMac, and still ship with “Fusion Drive”. Which is no where as fast as pure SSD.

    Basically I felt Apple no longer cares about the Mac.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.