Top 10 greatest IT chief executives

Last week, we looked at the geeks who created iconic technologies. This week it's the CEOs.

The chief executive is the rock star; they are the face of the company and the ones who are ultimately saddled with billion dollar decisions that can make or break entire markets and leave their staff either much richer or asking if you want fries with that.

So what makes a good chief executive? Leadership, both internally and to the world outside of the company is important. So too are brains, but not as much as you’d think. After all, leaders have geeks for that. Business sense is critical, but so too is knowing when to throw out the prevailing wisdom and follow your instincts.

One thing not needed is a charming personality. Many of the people on this list, particularly the top three, sometimes show the personal skills of a grumpy Attila the Hun and possess all the charm of a serious road accident. But maybe that too is something that’s needed in the corporate world; as legendary baseball manager Leo Durocher put it – “nice guys finish last.”

As ever this was a tough list to write, not just in whittling the possible candidates down but especially in their position on the grid, and we’ve included a couple of honourable mentions at the very end. There’s a lot of good talent in the software industry (and some absolute idiots, as next week’s list will show) and that’s a sign of how mainstream the technology has become.

10: Marc Benioff, Salesforce.com

Shaun Nichols: Legend has it that when Marc Benioff broke the news to Larry Ellison that he would be leaving Oracle to start up a web-based CRM service in the basement of a house in San Francisco, Ellison not only wished Benioff well, but he also in the company.

Since then, Benioff has taken Salesforce from a small startup to a legitimate force in not only the CRM field, but larger enterprise computing. Companies such as SAP who once mocked the software as a service model are now scrambling to release their own web-based offerings, and Benioff now finds himself going toe-to-toe with his old company's PeopleSoft branch, something he clearly relishes.

Iain Thomson: Benioff and his crew did as much as anyone to legitimise software as a service in the eyes of the industry. Now everyone’s at it, and it looks to be one of the more successful and profitable arms of IT in the years ahead.

Being so far ahead of the curve has its disadvantages as well. Being so convinced of their righteousness, and fighting against the weight of industry inertia, has left some Salesforce staff coming off like evangelists for a particular sect.

Benioff also gets credit for being a big believer in giving something back, to staff and the community at large. It’s a trend I wish more leaders would follow.

9: Meg Whitman, eBay

Iain Thomson: Meg Whitman managed to do what virtually no other dotcom chief executive managed in the 90s and beyond - run a profitable business.

She joined in 1998 after the founders realised they needed someone with commercial experience. Whitman was a professional, having held various high profile positions and was at the time in charge of, oddly enough, the global marketing of Mr Potato-Head amongst other things.

In her ten years as chief executive Whitman never once had a loss making year and grew the company from a 30 person crew making US$4 million a year to the it is today. From friends who’ve worked with her I also understand she was a real pleasure to work with and fostered a good corporate culture.

Whitman’s shown that you can be a great boss without being a total git about it, and provided a valuable example to others.

Shaun Nichols: Chief executives are a lot like politicians, in that the qualities that make them good at their jobs often make them insufferable to their subordinates and associates. It's always refreshing to see a successful executive who is able to connect with employees as well.

Whitman is among the few successful women leaders who emerged in a male-dominated dotcom boom, and is so well-regarded that she is considered to be a front runner for the California Governor's office in a few years, as well as having been touted as a possible running mate for John McCain.

8: John Chambers, Cisco Systems

Shaun Nichols: Chambers took over as chief executive, and later chairman, of a modestly successful network hardware vendor in 1995 and within ten years transformed it into one of the largest companies in Silicon Valley. A large part of that has to do with the explosion of the internet necessitating massive amounts of networking equipment, but Chambers' leadership also plays a large part.

Chambers often gets overlooked in comparison to other top execs. His Wikipedia entry is all of about three inches long for example. This is in part because network routers aren't exactly the sort of thing that gets people particularly worked up about, and Chambers has never had the eccentricities of a Larry Ellison or Steve Jobs.

But it's also because in his tenure, Chambers has managed to by and large steer clear of antitrust hearings, stock scandals and other embarrassing situations, something I'm sure his stockholders are grateful for.

Iain Thomson: That Chambers has been good for Cisco is beyond doubt, as too is the beneficial effect of the company’s products. Personally I wish they didn’t form the backbone of the Great Firewall of China but that’s business it seems.

But what’s also noteworthy is the way he’s made Cisco such a success. The Microsoft slash and burn approach to opponents isn't for Chambers. Rtaher, he has taken the second approach, if you can’t beat ‘em, then buy ‘em. It’s a much more civilised approach all round.

Cisco now forms a large part of the backbone behind the most important communications system in the world but instead of resting on his laurels Chambers continued to insist on innovation and research. It’s a sure fire way to future success.

7: William Hewlett and David Packard, HP

Iain Thomson: A bit of a cheat this one but seldom have two people become so inextricably lined in a business.

I think it’s fair to say that and Packard were the creators of Silicon Valley. The where the company was started in 1939 is now a national monument and the two took off from their humble beginnings to build one of the world’s biggest technology companies.

Talk to old timers in the business, those that are left, and they will appear slightly misty eyed about the good old days. It was organisationally a flat structure, a system years ahead of its time, with everyone getting their hands dirty. Famously there were only three actual offices in the building; one for Hewlett, one for Packard and one for one of the engineers who was so loud he put everyone else off,

The founders were referred to by employees and outsiders as Bill and Dave and the company formalised this open style in the HP Way – “a deep respect for the individual, a dedication to affordable quality and reliability, a commitment to community responsibility, and a view that the company exists to make technical contributions for the advancement and welfare of humanity.”

Sadly that spirit is gone now, subsumed into a money-making machine that I’m sure would the founders. But for its early history, and the excellence they showed in building it up, they are worthy members of the list.

Shaun Nichols: So much focus is put on the free-wheeling tech millionaire culture that has emerged in the last three decades that some of the people who actually built Silicon Valley are overlooked.

While the scientists and engineers of these eras are still revered, the businessmen who guided the development of these technologies are often passed by in the history books. So too it seems for Hewlett and Packard, who often seem remembered only for their initials.

Hewlett and Packard helped establish the relaxed, egalitarian culture that later became the standard in the tech world and, unlike many modern startups, they were able to do so while constructing a solid, sustainable business plan.

6: Michael Dell, Dell Computers

Shaun Nichols: While still in college, Dell founded his computer company and planted the seeds of its successful build-to-order sales method. As the internet bloomed in the 90s, Dell's direct sales method caught on with both consumers and businesses and turned Dell into the top PC vendor on the planet.

In 2007 Dell, like Jobs, was called back to head up the company after several lacklustre years. One executive who was present for Dell's first day back at the helm of the company later told me that as soon as Michael Dell entered the room for his first meeting, the entire company's changed for the better.

That is the very definition of a great chief executive: someone who can inspire the entire company by simply stepping into the office.

Iain Thomson: It must have been heartbreaking for Michael Dell to see the company that bears his name being run down after he left.

Dell was at the forefront of that most remarkable feature of the PC business, that every year prices fall and power increases. The commoditised buying process, vast build to order factories and the mass market sales techniques that Dell honed to a razor’s edge were so good that the rest of the industry copied them and prospered too.

As Shaun has pointed out, his return bodes well but he’ll need to do a lot to pull Dell back to the number one spot.

5: Frank Cary

Iain Thomson: Of all the chief executives on this list Cary is probably the one you’ve never heard of, but his influence on all our lives has been immense.

Cary was head of IBM from 1973 to 1981 and was the executive who took IBM from big computers to small ones. Now this in itself was a logical step but it is how he did it that showed true vision and greatness.

Back in those days, and to an extent even now, IBM was a strange corporate beast. Employees could only wear dark suits, white shirts and sensible ties. Everything was done in-house and there was a definite IBM way which must be adhered to at all times, with regular meetings, cost control and corporate unity.

But Cary recognised that this approach wasn’t going to work with the personal computer, or rather that it would, but would produce a terrible computer five years down the line and let Apple steal the march on his company. So he assembled a team of engineers and told them to go away and come back with a computer in a year, and he didn’t care how they did it.

This willingness to throw away an instruction manual he had been raised on virtually his entire working life (Cary joined IBM in 1948) is the hallmark of a great leader and without him we’d probably all be stuck using whatever Steve Jobs told us was cool.

Shaun Nichols: Cary took a bit of the starch out of Big Blue. Though it was still stuffy by the liberal, west coast standards of many other tech firms, IBM was able to bust out of its bureaucratic old-world mode and keep its position as a market leader.

Say what you want about IBM, for all of their old-school office values, the company has never lost sight of the cutting edge in its products, nor has it ever lost the tremendous amount of respect it commands in the industry.

4: Gordon Moore

Iain Thomson: Where to start with Moore? He was at the helm of Intel from 1975 to 1987, an astonishing run that saw the birth and puberty of the personal computer industry as we know it.

Moore used the same tactics to grow the company he co-founded as Bill Gates, making sure that his products were used as the standard right from the get go. He then advanced the chip technology steadily, with no false starts or compatibility problems so that there was really no sense in buying anything other than Intel microprocessors for a long time.

That said he wasn’t soft about it. His legal battles with AMD to keep them out of a market he saw as his were brutal and belie the cuddly image he has nowadays. While he may be primarily the engineering genius and hardcore geek there’s a steel spine under the lab coat.

However he will probably be chiefly remembered for ‘Moore’s Law’, which isn’t a law at all but simply a statement that microprocessor design is going to carry on improving at a steady rate. To an engineer it was pretty obvious but Intel has hammered it into its corporate culture (and the rest of us) to such an extent that if you play the ‘Moore’s Law Drinking Game at an Intel Developer Conference keynote you’ll be unable to walk out by the end of the session.

Shaun Nichols: Intel execs have turned Moore's Law into a mantra of sorts. The real genius behind the concept is that not only does it constantly provide a marketing buzzword, but it gives the engineers an ever-moving, yet tangible standard to reach with each new model.

Moore is also one of the few people to earn consideration for both the top geeks and top chief executives lists. So often the engineers and executives find themselves at odds about how to run the ship. That Moore was an for both sets truly underscores his genius.

3: Larry Ellison, Oracle

Shaun Nichols: Larry Ellison will make any number of short-lists of Silicon Valley icons. He is an iconic tech executive both in and out of the board room. He turned Oracle's database business into a reliable cash cow and later guided it into the enterprise software market.

Aside from overseeing the creation of one of the in the tech world, Ellison has also set the bar for how executives can in style. He owns a small army of private and ex-military jets, sports cars and luxury yachts. He runs an America's Cup sailing team and is so revered as an executive that fans of the San Francisco 49ers football team still lobby the club's owners to reconsider a buyout bid Ellison made several years ago.

Iain Thomson: Ellison is an idol to many in the business world for his intelligence, street smarts and business leadership. He’s a good man to have on your side, but a terrible enemy.

He’s a fighter in the business world, and there can’t be too many corporate battles that have ended up with the losing side having their chief executive gaoled. All this has left Oracle dominant in its field and Ellison very, very wealthy.

In interviews he can come across as a bit of an abrasive character, and his wild lifestyle has raised plenty of eyebrows. When it comes to celebrating his success Ellison is neither quiet nor humble. That said it’s not all vulgar excess, Ellison also gives away an astonishing amount of money each year.

2: Steve Jobs, Apple

Shaun Nichols: There was some debate as to whether Jobs should be at the top of the list. Ultimately, the clout of Gates won out, but that takes nothing away from Apple's visionary leader.

Jobs founded Apple in 1976 with friend (and number two geek last week) Steve Wozniak. Although Woz designed the computers, Jobs was the one who oversaw the creation of the company. He had a vision from the beginning of Apple bringing technology into people's homes, and has long been an advocate of blurring the line between the study and the living room.

Perhaps the greatest tribute to Steve Jobs is seen in what happened to Apple in his absence. After Jobs was ousted from his position at the company, Apple proceeded to go into a tailspin that included a parade of bad business deals and failed products. Jobs returned in 1997, and in less than a year the company was on its way back to a renaissance.

Though he is notoriously temperamental and hard to deal with, there is no arguing Jobs' midas touch in the tech world. After leaving Apple, he went on to found computer animation giant Pixar and software company NeXt, whose Unix-based system would later become the heart of OS X.

Iain Thomson: Shaun is ever the master of understatement, there was, to use a euphemism, a ‘heated discussion with a full and frank exchange of views’ over Jobs’ position on the list.

Successful as he is Steve Jobs comes across as the kind of man you’d either worship, or run barefoot over broken glass to avoid. He’s abrasive, egotistical and, according to some he’s worked with, a borderline sociopath.

But despite all that he is an excellent leader in some regards. He inspires some very good products (and a few bad ones - Shaun and I disagree on the success of NeXT) and gets the kind of perfectionist spirit out of his staff that shows what a good leader is capable of.

However, he does have one major black mark on his card – the lack of a successor. So keen has he been to consolidate his position that there is no obvious replacement and when he goes Apple will either implode again or be for years.

1: Bill Gates

Iain Thomson: tops out our list. It’s not because of his run as the richest man in the world, or his great philanthropic work, but because by spotting market trends and exploiting them he has built Microsoft into a software superpower.

Gates was never the great programmer or designer, but he works with a ruthless, almost autistic, focus that cuts through the competition like a Visigoth hoard after a particularly potent batch of mead. The software monoculture he forced on the industry has proved a blessing in disguise, allowing it to grow far faster than if there was true competition among operating systems.

He bluffed his way onto IBM’s PC program by rebadging another company’s code, developed so-so copies of popular applications that were just good enough to beat the competition and tied PC manufacturers into software contracts that would make Satan’s legal department blush with shame.

He’s also not the greatest visionary the industry has ever known. He famously wrote off the internet as a fad, before realising his mistake and getting in the game, leveraging his existing monopoly to again wipe out the opposition, a move that cost him hundreds of millions in fines and a permanently soured reputation.

Nevertheless Microsoft has gone from being a small BASIC coding concern to the most important software company the world has ever seen, in large down to his ruthless competitive spirit. Whether this comes from his family background or having his head flushed down the toilet one too many times by school bullies I don’t know, but my goodness it works.

Shaun Nichols: So the man is considered the Darth Vader of the tech world, and pretty much every executive in the business still has nightmares about Gates and company setting siege to their corner of the industry.

But you really do have to give the man credit. Even when his products appeared overmatched and his company outgunned, Gates found a way to bring one competitor after another to their knees.

Despite his evil image within the business, Gates' work outside of Microsoft has been anything but. Nobody on the planet has pledged to give more money to charity than Bill Gates, and the work of the Bill and Melinda Gates Foundation is making a very real difference in thousands of lives.

Honorable mention: Mark Hurd, HP

Shaun Nichols: Hurd cut his teeth in the midst of a nightmare scenario at HP. Not only was the company's business operation sputtering, but the corporate culture was in crisis. The reigns of Patricia Dunn and Carly Fiorina had created an air of mistrust in the board room that would later manifest itself in the infamous 'pretexting scandal.'

With his company needing a remake and several executives facing the very real possibility of prison time, Hurd a resurgence at HP and helped the company emerge from the scandal.

Iain Thomson: I had serious doubts about Hurd’s inclusion in the list at all. He at HP during the Patricia Dunn years, although the fact he came through it smelling of roses and now runs the show shows a certain talent. We shall be watching Mr Hurd very closely in the years to come. True, under his stewardship HP is now the number one manufacturer in the PC industry, the balance sheet is very healthy and his career at NCR is creditable but I have my doubts about his long term staying power.

Honourable Mention: Jeff Bezos

Iain Thomson: Jeff Bezos, founder and head of Amazon, was a personal choice for the list. While he was one of the most heads of the dotcom era Amazon was famous for not making money. Indeed, it only in 2001, seven years after its inception.

This is quite unusual in a world where venture capitalists generally their money back with interest in a few short years, but it is a strategy that served Amazon well, letting it ride out the dotcom bubble’s burst with relative ease.

Legend has it that Bezos scribbled the Amazon business plan down during a drive from New York to Seattle with his wife. Quite why it took him that long to write ‘sell stuff cheap online’ gives a lie to the legend but nevertheless Amazon is quite a success story, although it has yet to recoup its early losses.

But the second reason why I wanted Bezos on the list is that he is that rare commodity, an honest man. At the height of the dotcom bubble he was asked about the market’s valuation of his company. He said, on the record, that the stock was overvalued and he wouldn’t advise investors to buy. That was a gutsy move at the time and I respect it still.

Shaun Nichols: Where countless other good ideas bombed in the early days of the decade, Amazon managed to come out of the dot-com crash as a market force. The idea for Amazon was simple in hindsight, but Bezos was one of the few who managed to run the company well enough to emerge from a highly competitive and volatile market and become an icon.

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