In five years, Will Sterling has seen his role as CTO of The Island ECN change dramatically. And in that time, his tech expertise has helped Island grow into NASDAQ’s largest electronic securities marketplace, executing approximately one out of every five of the exchange’s trades. Island’s message traffic has grown by 2,679 percent since 1998, and Sterling continues to oversee the general tech strategy as well as development of Island’s core proprietary technology. In the end, he says success comes down to understanding your business. “Expecting your business leaders to run the business without your heavy involvement is not realistic,” Sterling says. “In most business, the distinction between technology and business is largely academic. In practice, the technology is the business, and trying to draw distinct lines between the two areas is a waste of time.” Managing constant change With the large volume of traffic Island regularly sees, Sterling finds that his role as CTO is partially defined by the requirements of the financial services market: “the critical nature of the systems, the real-time nature of the demands, the extreme pressure on project time frames, and the sheer magnitude of the transactions are expected to handle.” Yet Sterling says the basics remain similar to those faced by other CTOs. “Regardless of the business segment, I think one of the most important skills of a CTO is their understanding of the business itself,” he explains. “It’s much better to have a good understanding of technology and a good understanding of the business than to have a great understanding of the technology and a mediocre understanding of the business.” On the technology side, Sterling makes sure to keep system growth simple, avoiding placement of too much functionality and complexity onto a single system, which he says also makes upgrades and other changes easier because “each program is responsible for such a well-defined set of tasks that we don’t have to spend all of our time trying to figure out what a given change is going to affect.” The proprietary nature of Island’s technology also helps manage growth; although it takes longer to build the technology from scratch, it saves time when modifications are needed. Sterling points to Island’s data services project as an example of this: at first, components were built in JSP and run over JSP-supporting, third-party Web servers. “We immediately had performance problems because the Web servers couldn’t handle the number of requests they were receiving on the first day,” says Sterling. That led to a switch to an internally-written HTTP server. “It took some development work up front, but that platform is now the basis for nearly all of our data services applications, and we haven’t had a single capacity-related problem since we made the switch,” he adds. The proprietary systems also means that emerging, disruptive technologies have had little impact so far on Island’s business. “In my opinion, the most disruptive force in our business has been the dramatic improvements in cost and performance of computer hardware over the past 10 years,” Sterling says. But as financial services evolve, Sterling does see an area where .Net and similar Web services technologies will be useful to improve efficiency along the stock-ordering process. “If you look at the entire process, from the time an order is entered until the time when the stock and money is moved between brokers, that process is still a long way from being the streamlined, real-time process that it could be,” he explains. Growth challenges For a few years after Sterling joined Island in 1997 as its first employee, his role as CTO was very broad. “Back in 1998 when there were only four or five people at the company, I spent about half my day on the phone with customers while configuring Cisco routers to send out to subscribers,” Sterling remembers. Now, he has a technology group of about 70 people and isn’t regularly configuring routers these days. Because of Island’s proprietary systems and the learning curve associated with it, organizational growth is managed by “hiring very selectively,” which Sterling says helps keep turnover low and lets fewer people get more done. “Even if your business needs stay relatively constant, as your team grows you find yourself less needed in areas where you have the strongest people,” he explains. “Where you’re needed will usually not be consistent with where you most like spending your time, and it’s important to let certain day-to-day responsibilities go as you’re needed in other areas.” Sterling takes pride in working with his “incredibly capable team of technologists” and keeping Island’s technology strategy rolling forward. The company provides subscribers with a back-end system for displaying and matching limit orders for stocks and other securities, as well as other related services. To that end, the company’s systems have processed over 15 million messages a day at times. Island’s tech foundation includes datacenters and Intel-based hardware, usually running one or two processors over a distributed environment. Sterling says this means they can upgrade parts of the system “without having to replace huge monolithic systems that typically have huge monolithic costs associated with them.” Proprietary technology, created in-house, makes up much of Island’s core matching systems — the heart of its business. Other systems, such as those for front-end software and reporting systems, are written in Java running on Windows 2000 or Linux, Sterling says, adding that the company also uses a host of technologies such as JSP (JavaServer Pages), Microsoft SQL, and Kdb. But as with many CTOs, Sterling finds the technology demands and high-pressure environment aren’t always the toughest part of the job. The most difficult part of being a CTO involves time — specifically, the lack of it, he says. “Having to choose between so many things that I could spend my time on, but only having time for about 30 percent of what I’d like to get done is probably the least favorite part of my job,” Sterling explains. “Of course, that’s the one part that I know will never change for someone in my position.” — Stephanie Sanborn Software DevelopmentTechnology Industry