The Grill: Rosetta Stone CIO Pradeep Mannakkara makes a rapid move to the cloud

An IT reorganization and a move to cloud computing gave this CIO early wins.

When Pradeep Mannakkara took the CIO position at Rosetta Stone, he encountered an IT infrastructure that was nearly the same age as the 21-year-old language-learning company. So Mannakkara established a plan to not only update, but also transform Rosetta Stone's technology stack and its 70-person IT department. Since starting in 2011, he has shifted much of the aging infrastructure to cloud-based platforms and added more mobile applications and state-of-the-art technologies. He says the changes achieved his goals of enabling a more efficient workflow and fostering innovation, while also increasing the strategic value of the IT organization.

How did you change the company's outlook? We had to get some incremental wins. We had to look at what would help us grow our revenues. And I reorganized the team. We had a structure that was called Build or Run, and it was not very effective for articulating roles and responsibilities. So you now see what you'd expect in a technology-driven organization: [Elements such as] a data center services function, a Web engineer function. Our corporate systems function was spread out, so we separated our BI and enterprise architect functions. Then we said, "Who is each of your customers?" so there's a clear line and accountability. Once we got the trust and saw wins, we started moving one after another, pushing the next wave, which was into cloud.

What was your take on the technology infrastructure when you arrived? A lot of homegrown and early 2000s technology. The beauty was we were having to leapfrog, which worked out well. We moved to cloud in much more spaces than we would have if we were on other, newer technology. In this last 12 months, we've made a very rapid move to cloud.

What technology changes have you made so far? We did the Salesforce server cloud in April of last year. We moved away from Microsoft Outlook for email and went to Google for email as well as app storage. We've looked at other ways of obtaining cost efficiencies as well as driving more capabilities as we rolled out a slew of cloud-based technologies. We also looked at Dropbox and Box and other [file-sharing] services. We were finding out [workers in] remote locations as well as our marketing folks were setting up private Dropbox files to share material, and our engineering team was doing this, too. This could be corporate [intellectual property], and this is happening in companies all over the place, so we said, "We need a corporate solution." Now we're pushing Box as a standard. It's less to manage and it's all in the cloud, and they can work from anywhere.

And we went with Okta; it's a cloud-based single sign-on provider. Password resets were one of the biggest ticket items on our help desk, and with Okta they've dropped down to nothing. We also rolled out Concur for our employees who have to do expense reports. And for our commission system, we rolled out Xactly, which is built on the Salesforce platform.

What do you look for in new technologies? If things aren't simple, you're not going to have people using them. User interface is so important.

Do you still see benefits in on-premises systems? There are reasons to stay with on-premises solutions. I'd say, however, that a lot of those are fast disappearing. If I can get it done with the proper security faster and cheaper with cloud, I'd go for cloud because it has the value I look for. How much value I provide to my organization is based on how fast I can deliver. If I'm doing this on-premises and have to have a different set of resources to support it, but it's not adding the same value, then my organization doesn't win.

The other part of this, when you look at technology, three years is probably the amount of time you'll run it, and then you figure there will be something better. So I'm making things modular enough so I can swap out components. And you can do that easier with the cloud, because with SaaS you don't have all that hardware and software on the books. I've changed about 80% of my technology stack in the past two years, and a lot of this has moved to the cloud. But I've also brought some on-premises. For example, we use Magento for our e-commerce. We elected not to move this to the cloud at this time because it's so central, it touches so many systems. But at some point, would we consider moving to the cloud? Absolutely.

What is your biggest IT project now? We're doing things around data and reporting, and there are some exciting initiatives there. As for challenges, one that we've had is with the multitude of videoconferencing systems out there. There's Polycom in the conference rooms, people are using FaceTime and Skype and Google Hangout. We just signed with Blue Jeans. They're in the cloud as well. They allow you to do high-definition audio and videoconferencing.

How do you help lead transformation? It's really being part of that core team, being part of defining where we go as a culture. You can say, "I want to change it," but your actions dictate what happens. I try to listen and understand but also drive us to where I think we need to be. There are disciplines I use, but a lot of it comes down to listening and communicating and driving some of those uncomfortable conversations we sometimes need to have, challenging ourselves about what really needs to happen to help us have better outcomes.

-- Interview by Computerworld contributing writer Mary K. Pratt (

Copyright © 2013 IDG Communications, Inc.

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