The best CTOs of 2008

The CTO’s job can be both exhilarating and thankless. Exhilarating in that you get to explore new technologies and figure out how to apply them to create new business opportunities or solve thorny business problems. Thankless in that there’s always pressure to do more with less, solve the impossible, and get people to go along with change they may not appreciate the value of. The best CTOs use good people, the right technology, and management skills to meet business challenges.

To choose the winners, a panel of InfoWorld editors and Test Center analysts pored over more than 100 nominations from CTOs themselves and from our own contacts and pool of industry experts. We interviewed all the finalists before making our ultimate selections.

This year’s winners tackled all sorts of problems and used a variety of techniques, but we did see some clusters of commonality:

Going beyond the obvious Several of our winners took existing technology efforts and got new value from them.

Bud Mathaisel of Achievo started hearing customers of his offshore IT facilities were concerned about intellectual property protection, leading him to realize he could upgrade his existing security measures into a business advantage. At UPS, Dave Barnes applied the science of telematics to new aspects of vehicle and driver behavior, using workflow analytics to come up with new ways to save money and time while increasing driver safety.

At Transplace, Vincent Biddlecombe saw an opportunity to use a datacenter refresh effort as a platform for his company’s software-as-a-service offering as well. And at Lifetime Products, John Bowden realized that the use of thin clients could secure intellectual property at overseas facilities.

At Southern Polytechnic State University, Bill Gruszka realized that in his campus environment, a dictate-oriented policy on mobile and wireless security was untenable, so he reframed the problem and solved it in a new way that allowed device choice to continue. At Veracode, Chris Wysopal had long been obsessed with security, spending part of his youth in the “white hacker” community. That obsession let him perceive a very different approach to securing applications that formed the basis of his company.

At Digital Realty Trust, Jim Smith saw the advantages of green IT not just in its own datacenters but as something that needed to be championed globally — which he then proceeded to do via standards efforts — while leading the way at his own company. Sun’s Greg Papadopolous saw a similar challenge in the datacenter and initiated Project Blackbox both to help solve it and give Sun a renewed chance to compete.

Making the big initiative happen Many CTOs are instrumental in enabling a key business objective through the implementation of a key technology. This year’s CTO 25 winners had several such examples. For example, Virgin America’s Bill Maguire had to start an airline from scratch in just months, and to do so he made a risky bet on open source technology.

Greg Framke at ETrade Financial quickly developed a trading platform that let the firm expand into six countries, allowing multinational trading. MasterCard Worldwide’s George Spies took his SOA savvy and used it to launch a new global debit platform as a secret project. And Agito Networks’ Timothy Olson saw an opportunity for a new product offering that he then pulled off in just 20 months.

At Lehman Brothers, Hari Gopalkrishnan had to revitalize a moribund back-office system, which he used as an opportunity to introduce technologies such as grid computing and to increase analytics-based insights. Antelope Valley Hospital’s Humberto Quintanar inherited an IT environment in deep freeze, requiring a major effort to get the hospital’s technology up to snuff.

Matt Kesner at Fenwick and West saw a new business opportunity for his law firm, one that he could meet by reconceiving forensics technology into a service offering. At OhioHealth, Jim Lowder wanted to use digital signatures for health records, but first had to convince the state to accept the technology as legal.

A focus on management savvy The best technology does no good if you can’t get your users to adopt it, or your management to pay for it. Several winning CTOs used their people skills wisely to accomplish their technology goals.

For example, at the State of Alabama, Jim Burns used a tough-love approach to integrate the dozens of technology fiefdoms into common platforms so he could get a manageable baseline for adding new services for the citizenry. At FirstHealth of the Carolina, David Dillehunt had to keep nurses happy while addressing an inventory management problem.

Vivek Kundra of the District of Columbia applied a portfolio management model, using stock-market practices, to identify problem projects early and either change out their managers or kill them altogether, freeing up resources for projects that would have real impact. At Aflac, Gerald Shields had to rethink his IT budget management to get out of the “mother, may I?” game with the CFO.

At Avnet, Bill Chapman had to rescue an acquisition whose economic justification was threatened by a severe data-architecture incompatibility — but his real challenge was getting his team to be open-minded about legacy SOA services as well as the new employees. At WSO2, Paul Fremantle used what he calls a player/coach approach to help his team deliver a string of advanced products.

Georgia Aquarium’s Beach Clark’s key challenge was to provide — with an IT staff of just five people — a mix of general and specialty technology systems for his unique business. At Credit Suisse, David Reilly wanted to change the tenor of his discussions on his virtualization goals from technology-based to benefit-based. And Jon Williams at Kaplan Test Prep and Admissions had to get his team to stop developing applications in isolation and instead look at developing together using open source components — a major culture shift.