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Gimme Five: Industry Veteran and Advisor Rick Roy on Delivering Better Software, Faster

Rick Roy is a 34-year veteran of the technology industry and a strategic advisor to AHEAD. Throughout his career, he’s served as CIO and peer advisor to large enterprises in financial services, automotive, healthcare, pharmaceuticals, and professional services. He is currently Managing Partner of RER Advisors.

AHEAD’s EVP of Customer Success and CMO Tom Pohlmann sat down with Rick to get his perspective on the state of digital technology in the enterprise.

We’re bringing their conversation to you in a four-part Gimme Five interview series covering digital transformation, innovation, the role of infrastructure in both, and the imperative to deliver better software faster in the enterprise. The fourth and final of these discusses how IT teams can deliver better software, faster.

Tom: CIOs seem to be leaning towards automating functions like infrastructure and security in order to free their time to deliver new applications. Is this a common point of view among the CIOs you’re working with?

Rick: There’s certainly a desire to get legacy maintenance on autopilot, at a cost as low as possible. CIOs are using the savings in cost and talent resources to drive new initiatives. However, the key to this approach is getting the right service levels across IT service areas. For example, within the insurance industry there’s a lot of discussion about whether or not customers should be able to submit an online claim 24/7, even if the claims department doesn’t operate 24/7. There are different technical requirements and service standards if a company does or does not choose to offer customers the ability to upload a photo of the dent in their car any time of day or night. Digital service standards should always match the business need.

Tom: Over the past five years have you seen a change in the ability to provide higher quality software faster?

Rick: I think there have been improvements within IT, but not necessarily organization-wide. We still see a lot of situations where companies say they’ve implemented Agile Software Development and are able to do things in only weeks that used to take quarters. But if you really look at what’s going on, what they’ve done is changed the development methodology of their app team within IT. Often they haven’t really implemented Agile in terms of high-level business involvement and engagement in true sprints of projects within short time frames.

There is still a long way to go in terms of culture change around the business, not just within IT. Everyone wants things to move faster but not a lot of people want to be involved and engaged with that process. That’s why CIOs and IT as a whole have to demand engagement across the organization—moving fast requires everyone to be on the same page.

Tom: Are you a believer in DevOps?

Rick: I am a believer in DevOps, and even in DevSecOps to more fully integrate security. Getting things done across silos takes a lot of time and energy. DevOps done right really breaks down those silos and gets people from various teams to work together to deliver projects better and faster. However, I do think it’s a means to an end and not necessarily the strategy itself. It’s a way to break through those barriers and have things move more fluidly.

Read more from our series with Rick:

Part 1 on Digital Transformation

Part 2 on IT Innovation

Part 3 on The Role of Infrastructure in IT Success


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