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.

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