12 IT Challenges Facing CIOs in 2024 (+Overcoming Them)

11 IT-Related Challenges Facing CIO in 2024 (+Overcoming Them)

The CIO role was established in the 1980s, and back then, it was just a little different from the CTO—CIOs handled technical projects and the proliferation of technology inside enterprises. 

Nowadays, the role of the CIO is constantly in flux, especially as enterprises race to secure a place in emerging technologies like artificial intelligence, machine learning, big data, and other concepts at the core of digital transformation.

This article will help you understand some of the challenges facing CIOs in 2024, chart a course to tackle these IT and digital transformation challenges, and outline how to build a robust digital experience footprint.

What are the biggest IT-related challenges facing CIOs in 2024?

  1. Creating a digital strategy that balances various priorities
  2. Tying digital investments and transformation projects to organizational goals
  3. Reskilling and upskilling employees for a digital workforce
  4. Improving cybersecurity awareness, defense, and infrastructure
  5. Designing a better customer experience
  6. Integrating cloud technology stack and avoiding SaaS bloat
  7. IT and SaaS consolidation
  8. Driving digital adoption of SaaS investments
  9. Keeping up with cutting-edge technologies such as AI, machine learning, big data, etc.
  10. Building a digital workplace
  11. Dealing with supply chain issues
  12. Managing inflation and an economic downturn

12 Most Critical IT Management Challenges Facing CIOs in 2024

Here are the most critical IT-related challenges CIOs must overcome in 2024:

1. Creating a digital strategy that balances various priorities

There’s a tendency to get caught up in the buzz, chasing the next new thing or the latest shiny object—and in IT, there are many of those: shiny new SaaS vendors featured on TechCrunch, ProductHunt, or at an enterprise conference.

Whether AI, machine learning, big data, or the future of work, it’s easy to get distracted with your digital strategy and IT roadmap. Arguably, there’s a case to be made for experimentation in IT but taken to the extreme, splitting your focus will suck the life out of your digital strategy while you chase moonshots you’re unlikely to win.

How to overcome this CIO challenge

  • Create a dedicated budget for your core IT needs and another for experiments.
  • Plan out and map your technology roadmap.
  • Build a strong argument for new digital programs before making the leap.

2. Tying digital investments and transformation projects to organizational goals

Digital transformation has become a bit of a buzzword, and enterprises are becoming wary of vanity projects under that label. And it’s a justified concern since anywhere between 70% and 95% of digital transformation projects fail to achieve their targets or exceed their timelines or budgets.

If your company’s leadership can’t see a straight line from your digital investments to an increase in the company’s long-term goals, get ready to get your budgets slashed. This will, in turn, lead to a negative feedback loop where you shrink your operations even further, perform poorly, and get your budget cut again.

How to overcome this CIO challenge:

  • Avoid changing the scope of projects midway because of pressures from leadership.
  • Ensure there’s a clear need from most of your employees, clients, or partners before embarking on a digital transformation effort.
  • Ensure every digital project follows a strict roadmap.

3. Reskilling and upskilling employees for a digital workforce

Training and development, especially in medium- and large-scale enterprises fall under the HR department. But, since most of that training isn’t classroom-style lectures, they partner with IT to choose and deploy learning management systems to upskill employees at scale. That creates a lot of questions, such as:

  • How do you train employees at scale?
  • What tools can you use to track your employees’ proficiency over time?
  • What employee training methods are most advisable, especially in a digital workplace?

How to overcome this CIO challenge


Above: Enable your employees with contextual user support and accelerate IT adoption with Whatfix's digital adoption platform.

The Whatfix Digital Adoption Platform empowers IT teams to create in-app guidance and self-service user support on all internal desktop, web, and mobile applications. Enable employees with Self Help, which overlays onto your CRM, HCM, ERP, CPQ, and other digital workplace applications. Self Help connects to your process and IT documentation, LMS, video tutorials, onboarding documents, and other IT support-related content to provide employees self-help, at the moment of need. Create additional in-app guidance and pop-ups to contextually guide users through applications and alert them to process changes.

4. Improving cybersecurity awareness, defense, and infrastructure

According to a report by IBM & Ponemon Institute, the average total cost of data breaches in 2022 was $4.35 million, up 2.5% from $4.24 million in 2021. And the scale of the threat—malware, ransomware, DDoS attacks, and phishing has only increased.

Sadly, ISACA’s 2022 State of Cybersecurity report shows that 62% of organizations feel their cybersecurity teams are understaffed while 60% have trouble holding onto qualified staff when they manage to hire them.

CIOs will spearhead the way against cyber threats, but from every indication, the average CIO is usually under-resourced in this area until an actual attack occurs.

How to overcome this CIO challenge

  • Build an A-class team of cybersecurity experts within your company and outside (consultants).
  • Provide cybersecurity training to your employees on detecting joint social engineering & phishing techniques.
  • Compartmentalize your technology infrastructure so that a single threat surface doesn’t endanger your operations.
  • Back up your data across geographies to aid business continuity in case of regional attacks.

5. Designing a better customer experience

According to Foundry’s 2022 State of the CIO survey, 57% of IT leaders surveyed stated that improving customer experience was a priority for them, while 81% said that they were implementing new technologies to support customer interactions.

But, that can be a significant challenge because of a bunch of reasons: first of all, since CX is often a distinct function in larger organizations, CIOs often face opposition from CX teams; C-suite leaders may get distracted with shiny new initiatives; and the data required to push digital customer experience projects may be lacking.

How to overcome this CIO challenge

  • Measure the impact of your CX efforts with your NPS, polls, and surveys.
  • Use product analytic tools and behavioral analytics tools to observe your customers’ usage patterns.
  • Build cross-functional teams that can work together across departments.

6. Integrating cloud technology stack and avoiding SaaS bloat

Growing companies often have a self-managed purchasing structure where an employee can whip out an expense card and subscribe to any SaaS product or newsletter they think is relevant to their work—with little oversight from the accounts department.

While it’s admirable giving employees autonomy, that decentralized structure often creates more problems than it solves since it leads to:

Since there’s no one place to see the entire organization’s SaaS footprint, redundant & unused subscriptions linger and cost companies anywhere between thousands and millions annually.

How to overcome this CIO challenge

  • Create stronger permissions workflows for purchasing SaaS & restrict rogue purchases.
  • Routinely go through your SaaS subscriptions to cancel shelfware and any unused subscriptions.
  • Make sure your licenses match your needed usage volume.

7. IT and SaaS consolidation

As we previously mentioned, 25% of SaaS spend is wasted. While much of this is general SaaS waste and poor buying governance, many enterprises face a SaaS redundancy problem.

Take a large, global enterprise as an example. Over time, mergers and acquisitions occur, each with its own SaaS products and digital tools. Regional offices and departments become fragmented, with their own processes and tools. Subsidiary companies operate completely independently.

When this happens, organizations inevitably pay for redundant applications that accomplish the same task.

We recently interviewed a CIO of a multinational food & beverage company with 80,000+ employees. They were using 45 different ERP systems across its 72 subsidiary companies. To add to this issue, it had different ERP processes for each geographical regional department (ie. the North American procurement division operated differently than the Middle East division.)

The company desired to consolidate all of these departments, teams, and subsidiaries into one ERP system. While reducing IT costs was a reason for the ERP consolidation project, it was also being prioritized to streamline workflows, centralize data, and make smarter decisions.

To overcome redundancies in your IT stack, you can:

  • Build software stack governance processes and teams.
  • Conduct quarterly or annual SaaS and technology stack health.
  • Offboard redundant software applications and migrate users to one system.
  • Use in-app guidance tools to facilitate smooth transitions and drive user adoption.

8. Driving digital adoption of SaaS investments

According to the 2020 SaaS trends report, the average company wastes around $135k annually on SaaS tools they don’t really use while Gartner estimates that as much as 25% of SaaS spend is wasted or heavily underutilized. In many cases, it’s not just an adoption problem—it’s a misspending issue since your onboarding and training resources can only encourage adoption if your employees are buying SaaS that they actually need.

Plugging up that SaaS leakage can extend your IT runway, give you back more budget to experiment with, and increase your organization’s financial health.

So, you can take two courses of action: either you get your employees to use the software they buy judiciously, or you limit their ability to subscribe to the new shiny app featured on TechCrunch on a whim.

How to overcome this CIO challenge

  • Conduct in-depth research before purchasing SaaS products.
  • Use product tours and guided walkthroughs to explain each SaaS tool’s UI to your employees and drive software adoption.
  • Maintain content libraries where employees can access explainers, videos, and product docs on-demand.
  • Invest in enterprise service management to provide high-quality IT service delivery and support to your employees.

9. Keeping up with cutting-edge technologies such as AI, machine learning, big data, etc.

For the past two decades, artificial intelligence was amusingly like nuclear fission—a usable, market-driven breakthrough was always 20 – 35 years away.

But now, ChatGPT has knocked down all those assumptions and started an arms race of sorts. For instance, after playing second fiddle to Google since 2009, Microsoft’s Bing search scaled up to 100 million daily users, just weeks after it rolled out an AI-powered search chatbot. Almost immediately, companies like Salesforce (Einstein GPT), Snowflake, Instacart, and Uber have either released its commercially available AI products or integrations with the GPT platform.

As a CIO, it falls on you to draft a course of action for similar emerging technologies, guide it through execution, and justify an expense made on it so that the C-suite can sustain it with the budget needed.

How to overcome this CIO challenge

  • Coordinate with HR to start building an experienced in-house team.
  • Focus on developing emerging technology solutions your business stakeholders can use, i.e., take AI & machine learning out of the lab and into the office floor.
  • Explain your objectives in clear terms.
  • Pair your programs with a robust onboarding and learning experience to carry everyone along.

10. Building a digital workplace

A digital workplace isn’t yet another buzzword for having endless meetings on Zoom & constant interruptions on Slack—actually, it refers to an environment where an organization’s staff can share information, communicate, and access the tools they need to do most of their work digitally.

And, while 87% of businesses believe digital will disrupt their industry, just around half (i.e., 44%) are prepared for that disruption, according to Deloitte, while 38% of American employees say their employers have not invested in digital transformation because of the cost.

So, while the responsibility falls on the CIO to unlock innovations such as AI, ML, and citizen development, they’re often starved of budget and support by the C-suite.

How to overcome this CIO challenge

  • Create clear proposals tying your digital transformation KPIs to overall organizational goals, such as increases in revenue.
  • Build robust onboarding and training programs to ensure employees adopt the digital workplace tools you release.
  • Provide employees with an IT self-service portal for resolving support issues independently. 

11. Dealing with supply chain issues

Supply chain issues seem like a distant concern for most employees that don’t deal with hardware—but whether it’s delayed shipments (thanks to port congestion) or supply shortages (GPUs, etc.) due to draconian lockdown policies in places like Shenzhen or Shanghai, no role feels the pinch harder than the CIO function.

How to overcome this CIO challenge

  • Diversify your suppliers geographically and create channels for substitutes.
  • Use procure-to-pay and procurement software to minimize logistical issues in your procurement pipeline.
  • Hold more inventory locally, i.e., change your purchasing model from just-in-time to just-in-case.

12. Managing inflation and an economic downturn

Most Western economies have witnessed record increases in living costs since 2020 due to central banks’ inflationary policies that saw inflation levels more than double from 3.5%. Now, with tighter fiscal policies in place, inflation is expected to fall from 8.8% in 2022 to 6.6% in 2023, according to figures released by the International Monetary Fund.

And we can’t discount the effect of the past 24 months on the market’s sentiments—with all the money that’d been sloshing around the economy, salaries for developers (and other technologists) skyrocketed while the average B2B SaaS vendor increased their pricing by 11% – 16% (i.e. four times higher than inflation) to protect their bottom line from rising prices across the wider industry, higher personnel costs, and a changing macroeconomic environment.

But now, the tap is drying up: between September 2022 and March 2023, technology companies have laid off 250,000 employees, and even giants like Google, Meta, and Amazon have slashed a significant portion of their workforce to cut expenses.

How to overcome this CIO challenge

  • Cut your SaaS expenses, eliminate shelfware, and consider switching to an on-premise or a managed service model, if you can justify it. Currently, the average company spends 12.7% (i.e., $1 out of every $8) of its budget on SaaS & if you can make a strong argument, it’s an easy way to slash your expenses. For instance, Basecamp expects to save $7 million in five years by moving its infrastructure from AWS to a managed services model. They’d been spending $3.2 million on cloud services annually, but with that single move, they’d be able to slash costs by 23% annually.
  • Create a stronger approval workflow for IT purchases.
  • Build an in-house team if you have the scale, or stick with long-term contractors if you’re smaller.
Overcoming IT challenges with Whatfix’s in-app guidance, on-demand support, and product analytics platform

Whatfix is a digital experience platform designed to help enterprises increase production adoption, democratize support, and build better customer experience using analytics. Our DXP takes a three-pronged approach to overcome IT challenges:

  • In-app guidance: Teach your employees, partners, and clients how your applications work using guided tours, product walkthroughs, and contextual cues like tooltips and hotspots
  • On-demand support: Maintain a library of product documentation, videos, and explainers where your employees can access self-help resources quickly, and
  • Product analytics: Track clicks, mouse movements, and action completions to understand customer experience challenges
What Is Whatfix?
Whatfix is a digital adoption platform that provides organizations with a no-code editor to create in-app guidance on any application that looks 100% native. With Whatfix, create interactive walkthroughs, product tours, task lists, smart tips, field validation, self-help wikis, hotspots, and more. Understand how users are engaging with your applications with advanced product analytics.
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