Successful tech startups offer IT tips for CIOs

Successful technology startups are usually keen to draw attention to their hot products, not to their internal use of IT. But companies such as Groupon,, Zendesk and SlideShare can offer CIOs lessons from what they’ve accomplished with limited resources, a blank slate for IT infrastructure and their finger on the pulse of the latest IT tools and services.

Groupon: IT integrated with business strategy

Groupon, the online coupon phenomenon founded in 2008, considers it crucial to its success that its IT officials establish close and frequent collaborations with business managers.

“We try to create a very collaborative environment, getting engineering very embedded with the business side,” said Ivan Moscoso, Groupon’s director of engineering. “There are never really strong divisions between our departments. We try to keep things fairly fluid.”

By having a lot of “face time” with managers in departments like sales, editorial and customer service, IT staffers can develop IT services and tools that truly support the efforts and goals of the company, Moscoso said.

To accomplish this, Groupon is very selective when hiring IT professionals. It looks for candidates who are strong on a technical level, but also able to understand the company’s business needs and to communicate well with non-IT colleagues.

“To get that close collaboration between the business and engineering means selecting the right people who can be both extremely technical as well as open to working with mixed, multidisciplinary teams,” Moscoso said.

Zendesk: Managing app-dev collaboration

Zendesk, which makes Web-based help desk and support software, holds internal “hackathons” for its application developers, which helps spur innovative thinking and gets valuable projects under way quickly.

The company holds brief “stand up” meetings for its application developers. Those last between 15 and 20 minutes and give the team a chance to discuss what’s new and bring up issues that need to be addressed. But for real sit-down collaboration, there are the hackathons, where developers work on manageable projects that can be completed in 24 hours, said Zack Urlocker, Zendesk’s chief operating officer.

“You don’t want to necessarily do that all the time, but sometimes that’s a nice way to get a bunch of small projects finished all at once and give people that sense of accomplishment,” he said.

Box.Net: Going to the cloud to keep infrastructure investment lean

The use of cloud-based applications and IT infrastructure services also tends to be popular and broad among technology startups, which say that it has allowed them to keep purchasing and maintenance costs down, while letting them focus on developing their unique commercial products., a provider of hosted content management, collaboration and file sharing applications, had until recently only one person devoted exclusively to IT matters — supporting 150 employees — thanks to its liberal and savvy use of cloud-based applications and infrastructure services.

“I’m working on things I would have never worked on before if we didn’t have this cloud infrastructure. I’d be doing repetitive maintenance tasks,” said Jeff Sutton,’s IT lead, and until recently the company’s only IT staffer. The company just hired a second IT professional.

For example, Sutton is in charge of the company’s internal application development environment, and of a VMware project. “There are a lot more things I have bandwidth to do. It gives me more time to focus on new technologies,” he said.

Aaron Levie,’s CEO and co-founder, said the company looks for cloud-based applications for everything, especially for standard IT needs. “We want to free up resources to solve the higher-order issues around technology,” Levie said.

This has also allowed to grow its staff very rapidly, sometimes doubling it from one year to the next, without having to hold back for fear of having its IT infrastructure buckle or collapse. “One of the breaking points when an organization grows like this is that their IT infrastructure begins to have challenges. We try to remove as many of those kinds of limits as possible from how quickly we can grow,” Levie said.

Like, Zendesk also uses a broad array of cloud applications and IT services, and that has allowed the 70-employee company to not even have one person devoted exclusively to IT.

“The reason why we can do that is because of the technology choices we’ve made, because of the cloud,” Urlocker said. “We run most of our business off of hosted, cloud-based software.”

In addition to using its own cloud-based application, Zendesk also uses business software from, Google,, Amazon Web Services, Rackspace and Yammer, in addition to Skype for most of its voice communications.

Asked about concerns many CIOs and IT managers still feel about cloud applications and services, Urlocker said cloud vendors have significantly improved their security, reliability and performance. “Things have really matured in the last few years. It’s not the Wild West anymore,” he said.

CIOs may find that the reliability and security they get from their commercial cloud vendors often exceeds what they get from their own IT departments, he said.

Urlocker recommends starting small and slow. “Organizations should start and take a few steps in this direction and try a few projects,” he said.

“If you have an IT organization that isn’t running any cloud-based software, that’s really behind the curve,” he added.

SlideShare: Software as a work in progress

SlideShare, a site for posting and sharing business-related presentations, has perfected the art of constantly tweaking its software and pushing out multiple changes per day based on continuous and exhaustive analysis of user behavior.

SlideShare’s CTO and co-founder, Jonathan Boutelle, recommends an approach of constant iteration with respect to software development, based on careful analysis of user behavior. “When you chop work into small enough chunks it becomes much less intimidating,” he said.

This approach is much less risky than the conventional philosophy of spending six months or more on a major IT project and then deploying it in full one fine day in a “big bang” manner, he said.

“We don’t like big bangs. We like to constantly make small changes and feel that’s a great way to reduce risk,” he said.

SlideShare is at the point now that it tweaks its Web-based application dozens of times per day. “The combination of having very good measurement of user behavior with the ability to make small changes to the site means we can iterate extremely quickly,” he said.

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Jim Love, Chief Content Officer, IT World Canada

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