On the sixth episode of Enterprise Software Innovators, Ravi Malick, Global Chief Information Officer at Box joins the show to discuss his storied career, which has spanned several industries and given him a variety of unique perspectives. Ravi’s experience has seen him work in investment banking and consulting and also the energy industry, where he spent nearly 4 years as the SVP and CIO of Vistra Energy before recently landing at Box. Ravi uncovers the operational differences of startups vs. Fortune 500 companies and how they can work together, the ways successful leadership teams are built, and how CIOs can most effectively lead new technology initiatives within their organization. 

While many larger enterprises might appear sluggish and hardly at the vanguard of innovation, Ravi’s experience at Vista Energy tells a different story. As CIO, he was able to lead Vistra’s implementation of a startup mentality: “We were in a Fortune 500 company, but there was a lot of startup feel to it…we were building things and testing new things…And through that, we were mov[ing] everything to the cloud. It was pretty fast paced and there really wasn't much of a dull moment ever.”  By shepherding a startup-infused mindset of growth and experimentation, Vistra was able to move forward from a regional, Texas based operation to a company with a national footprint. 

Moreover, Ravi’s desire to partner with startups early in their life cycle has consistently paid dividends for the businesses he’s worked for in addition to the startups themselves. Like any symbiotic relationship, the path of a Fortune 500 enterprise collaborating with a startup is a two way street. The enterprise gets early and often less expensive access to exciting new technology that can help propel them forward, and the startup gains valuable exposure, feedback, and insight into how to make their product better. In many ways, there’s nearly no better venue for a startup to gain critical, early stage feedback, while an enterprise customer gets to leverage exciting new technology. In the best case scenario, both sides are benefiting from these relationships.

While Ravi rightly recognizes the risks in working with early stage startups, he’s quick to point out that oftentimes, the risk is a misconception: “…you hear things like ‘what if they go under, what they go belly up, what if they get acquired?’ If you think about it, realistically, that risk exists with any business.” And while risk mitigation is crucial for any business, Ravi ultimately believes in the potential of partnering with startups more, because as he puts it, “I’ve always felt if you could use technology effectively, you could skip four or five steps.” And in real terms, those four or five steps not only bring about a positive change to a company’s bottom line, but also have immeasurable impacts on the culture of an organization. 

Before landing at Box, Ravi spent nearly a decade in the energy industry. As CIO, he was watching the two separate parts of the business working at different speeds when it came to experimentation. Rightfully so, the generation side (whether coal, natural gas, or solar) had a strict operational infrastructure because safety is a vital concern at all times. On the retail side, the technological demands meant that experimentation was critical to ensuring Vistra was keeping up with the times. While challenging, it provided Ravi with a roadmap for how CIOs must navigate environments with what he calls “multiple personalities.”

With his myriad experiences, Ravi has a unique perspective on the role of CIOs more broadly within organizations, being sure to emphasize elements of the job that are less celebrated, but still crucial to success. While a CIO and CTO is certainly judged on how they help bring about new technological initiatives to a company, Ravi believes operational innovation is important to spotlight as well. It’s a lesson he says has been reinforced over the years in various roles: “One thing I’ve learned over the years is that you can't build on a shaky operational foundation. All you hear about is the innovation and ‘we built this and we did that.’ But you don't hear about, ‘I took my infrastructure outsourcing from 20 million to $0, and from 300 people to zero.’ ‘Well, how'd you do that?’ ‘I innovated to do that.’ So operational innovation can be just as important as the business, revenue or growth innovation [in an organization].”

Ultimately, CIOs must walk the same tightrope that all members of the C-Suite do; the balance of technical prowess with the ability to be a leader. An ideal CIO has the knowledge and skills to effectively harness the power of the engineering team while also establishing the right culture and fit. Especially on the IT and technical side of things, a CIO must recognize that some technologists on their team want to remain on the front lines developing code instead of becoming a manager themselves. As Ravi puts it, “[being a successful CIO is knowing] the balance of understanding the characters of people and putting the right mix together.”

Listen to Ravi's episode here and read the transcript here.