That is a serious problem because, unless the selling company is incredibly large and diverse like, say, IBM, HP, or EMC, its very difficult to sustain an enterprise sales effort. The margins are very tight, the expectations (read: costs) are relatively high, and, if you screw up, the results can often be material within a month or quarter. Lots of risk coupled with very little profit, not exactly your Harvard Business School best test case.
Be that as it may, companies like Netscape, Sony, and Google who should (or should have) known better, continue to chase that market, and Apple is positioning to once again go after this elusive goal. But, going after the enterprise has little to do with the product; it has everything to do with the approach and having enough patience and/or money.
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Apple faces three critical weaknesses when it comes to Enterprise sales, though they just may have fixed the fourth. (And some argue passionately there is a fifth, prejudice against Macs, but I wont go there.)
The first is they dont partner or share well. Enterprise buyers want their vendors close, and when they arent, customer satisfaction and vendor displacement events occur very frequently. They demand road maps and want some say in future products, and if it is a government account, actually want some say in your employee mix, security, and quality metrics. Particularly if they are government account, they demand most favored nations clauses in contracts which assure them the best price and even want to constantly check your books as a result. Finally they demand an impressive amount of support, something Apple is apparently not even equipped to supply. Apple is far from the most sharing company and typically wont even acknowledge most of these demands.
The second is enterprises have policies that make it very difficult to sole source anything. They want competitive bids because without them they cant show auditors they actually did get the best price and that nothing underhanded was done for the vendor to get the business. Originating from the belief that there is active bribery (not as uncommon as you would think) in the vendor bidding process, a sole source agreement is an immediate audit flag and enterprises want vendors who can bid against each other. Apple, after the first bid, is the only vendor who supports the MacOS, nearly assuring a sole source arrangement after the first year (which can be bid competitively).