Retail IT Connect US 2025

August 04 - 05, 2025

Chicago Marriott Downtown Magnificent Mile

The Five Biggest Challenges Facing Retail CIOs

Brought to you by WBR Insights

When you come on board with a new company as a Chief Information Officer, there is a ton of work to get your head around. Hitting the ground running means understanding the biggest issues you're likely to face and meeting them head-on.

The role of the CIO has expanded massively in recent years. The rapid expansion and implementation of digital technology have meant these hard-working individuals have significantly more information to deal with than ever before. Whether it's effectively storing and processing the huge swathes of data your organization owns or ensuring that their budgets are spent with the best possible ROI, the role of CIO is an intense and rewarding one.

To help fresh CIOs on their way, we've compiled the top five challenges facing the role today. Conquer these challenges in 2020 and you'll be well on your way to success.

#1 Getting a handle on data

It is predicted that over the next five years, the amount of data generated, used, and stored by our global society will increase fivefold to 175 zettabytes (equivalent to a billion terabytes or a trillion gigabytes). However, this dramatic increase in data volume is leading to some CIOs overreacting and not dealing with the situation appropriately.

Many CIOs think they have to create large and all-encompassing data projects to help them deal with the huge amounts of data they are responsible for, but this is simply not the case and can lead to wasted time, money, and resources for very little beneficial return. A far better option is to break these projects down to tackle individual issues and tick them off one at a time.

"Most companies are wallowing in data, thinking they've got to create massive, proprietary data projects that are going to solve everything," said the former CIO of AIG and Kaiser Permanente. "Such in-house projects just give you basic insight about the data you own."

#2 Breaking down silos

It's hard to believe that in 2019 we're still talking about breaking down data silos. But it seems this is an issue that is not willing to go away anytime soon.

According to one survey, of the 97 percent of organizations currently going through digital transformation, 84 percent are being held up by data integration issues. Nearly half of all respondents have over 1,000 applications being used across their business, but a mere 29 percent have achieved successful integration - trapping valuable data in silos and creating woeful inefficiencies.

New data privacy regulations are making it harder than ever to do what needs to be done regarding data, but CIOs must focus on finding new ways to break down these silos while remaining compliant.

"You've absolutely got to create or adopt systems that help you comply with the law and still help you get the job done that you're trying to do," said former CIO of Microsoft, the Walt Disney Company, and the U.S. Government, Tony Scott.

#3 Risk

The CIO role is one that is traditionally associated with cold hard facts and scientific decision making. While this is obviously a solid ground on which to build, a side effect of this logical approach is that it can make CIOs somewhat risk averse.

However, in today's fast-moving and highly competitive environment, CIOs must find new ways of introducing ideas or find themselves lagging and struggling to continue to justify their role in the organization.

"In this day and age, you absolutely have to find ways to introduce new ideas," said former CIO of BP, John Leggate. "There's a craft to knowing where to start - how to do it, who you talk to, where to come in from, etc. - and if you have that skill or can develop that skill, you'll be in a much better position to succeed."

#4 Real-time engagement

With so much data flying around, one massive challenge for CIOs is finding ways to deliver that data to the people who need it. Once data has been transformed into actionable insights, getting that data into the hands of decision makers in a timely fashion will help drive real value.

"Data is the lifeblood of your entire organization," reports Forrester. "It should enlighten every function of the business, including CX, operations, marketing, sales, service, and finance. A data management strategy is critical. The goal should be clear: Provide all business functions with quick and complete access to all the data and analytics that they need, both now and in the future. But it's easier said than done, and that's where strategy comes in."

#5 Embrace Technology

Finally, CIOs need to continue embracing the range of digital technology out there and use it to support all other operations. Gartner research into government CIOs revealed that ten percent have already deployed an AI solution, 39 percent say they plan to deploy one within the next one to two years, and 36 percent intend to use AI to enable automation, scale of digital initiatives, and optimize the reallocation of human resources within the next two to three years.

AI is not the only technology either, with the Cloud (19 percent) Internet of Things (7 percent), and Mobile, including 5G (6 percent) all being widely considered for implementation.


These five challenges and more are all set to be hot topics at Retail CIO Connect 2020, taking place in February at Fort Lauderdale, FL.

Download the agenda today for more information and insights.