Contributing writer

10 most difficult-to-fill IT roles — and how to address the gap

Jul 18, 202312 mins
HiringStaff Management

Struggling to fill cybersecurity, AI, and data analytics roles, IT leaders are embracing new approaches to growing internal capabilities and rethinking talent acquisition and management strategies.

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Credit: Shutterstock / Jacob Lund

The CIO’s biggest hiring challenge is clear: “There is simply not enough talent to go around,” says Scott duFour, global CIO of business payments company Fleetcor, for whom positions in areas such as AI, cloud architecture, and data science remain the toughest to fill.

This enduring talent gap has been a pressing concern for years, says Max Chan, CIO at global electronic components distributor Avnet, but it is widening. “As technology continues to advance at a rapid pace, the demand for qualified individuals has soared,” Chan says.’s 2023 State of the CIO survey recently zeroed in on the technology roles that IT leaders find the most difficult to fill, with cybersecurity, data science and analytics, and AI topping the list.

  • Cybersecurity: 22%
  • Data science/analytics: 22%
  • AI/machine learning: 20%
  • Robotic process automation (RPA): 18%
  • Enterprise architecture: 18%
  • Application development: 18%
  • IoT/edge computing: 17%
  • Legacy technologies: 17%
  • Cloud architecture: 17%
  • Multicloud management: 17%

Exacerbating this issue is the fact that today’s CIOs are competing in a global talent marketplace, pitting them against higher-paying tech companies across geographies for new hires. 

“The talent out there realizes they have more options than they are used to, and they can leverage that to their advantage., Chan says. As a result, many enterprise IT leaders find themselves in bidding wars they’re unable to win. 

“The biggest challenge is finding talented team members at the market rate,” says Patrick Isaac, CTO at Accuro Solutions, adding that the current environment demands more intensive recruiting efforts. 

Geographical nuances are also arising. For example, Savio Lobo, CIO at managed service provider Ensono, finds talent more readily available in the UK and US than in years past, while hiring in India is as difficult as ever. But, notes Lobo, “in all geographies, finding well-rounded leadership and experienced technical talent in areas such as legacy technologies, cybersecurity, and data science remains a challenge.”

The net result? CIOs must up their talent game across the board, including talent management, engagement, training, and retention, in addition to hiring.

“Addressing these challenges will require a multifaceted approach that focuses on talent development and retention while adapting to the evolving needs of the industry,” says Chan. talked to IT leaders across industries about their hardest-to-fill IT roles as well as their best advice for meeting critical talent demands in the years ahead.

Grow your own cybersecurity expertise

With the cyberthreat landscape continually evolving, cybersecurity roles remain the hardest to fill. “We need professionals with up-to-date knowledge and specialized skills in this area,” Chan says. “The demand for these professionals is outpacing the supply of talent out there.”

The 2022 ISC2 Cybersecurity Workforce Study calculated a cybersecurity workforce gap of 3.4 million professionals. To get the skills they need, IT leaders may have to play a longer game, focusing on lifelong learners and developing depth of experience in-house. 

“Organizations should look to hire and train fresh graduates instead of searching exclusively for experienced professionals,” says Sourya Biswas, technical director for risk management and governance at global cybersecurity consultancy NCC Group. 

Swamy Kocherlakota, executive vice president and CIO for S&P Global, recommends a proactive approach of “upskilling or cross-skilling junior talent to prepare them for the future of work in technologies that are going to be critical going forward.” These include not only cyber, but also cloud and generative AI, he says.

AI and data science dominate the agenda

As companies proceed with digital transformation efforts, their focus is firmly on enabling business outcomes with data, increasing demand for data science, analytics, AI, and even RPA skills. “With the entry of ChatGPT and other generative AI, we expect the demand for data science, AI, and machine learning to further surge in the coming time,” says Aamir Khan, senior analyst at Everest Group.

S&P Global, for example, is entering its AI 2.0 era. “If we’re looking to build, train, and run models at scale to run in parallel to each of our products, we need talent who can help us unbundle the data by refactoring apps and data, and building a scalable data fabric that is flexible to feed to a generative AI platform,” says Kocherlakota, who is seeking AI experience and generative AI knowledge.

But, Kocherlakota says, “generative AI technology is nascent and best practices are still evolving.” Only a few professionals have had the opportunity to drive this at scale; as a result, top talent is going to be in demand across industry players. S&P Global also needs complementary skills in software architecture, multicloud, and data engineering to achieve its AI aims. 

“It can still be a challenge to find[IT pros]s versed in architecture with a practitioner’s mindset, building with the right abstractions to future-proof our investments,” says Kocherlakota.

At Merchants Fleet, building out a modern data and analytics infrastructure to support the fleet management solutions provider’s hypergrowth over the past three years has been a top priority. To create a 360-degree view of its clients and visibility into the end-to-end client cycle, Merchants Fleet is seeking data science, analytics, RPA, and machine learning skills at a high volume. 

“We have learned to think and act quickly in our efforts to attract and retain top talent in these areas,” says Jeanine L. Charlton, Merchant Fleet’s senior vice president and chief technology and digital officer, noting that she has been able to tap into talent from around the globe. “This includes aligning our compensation practices to be competitive on a global playing field, as the compensation scale for tech has accelerated far beyond many other talent segments.”

Flexing to meet wid-ranging needs

CIOs’ lists of hard-to-fill roles include not only leading-edge areas like AI, data science, and IoT/edge computing, but also IT mainstays such as application development and legacy technology skills.

One approach to meeting such wide-ranging needs is to cross-train and give employees the opportunity to learn and work across capabilities, Charlton says. 

“Merchants is investing in all our systems, so candidates have an opportunity to work with a very rich tech stack, and a combination of legacy and emerging technologies,” she says adding that, because the company has a good deal of proprietary technology,she is always looking for candidates open to learning new things. Ultimately, IT pros energized by that variety are more likely to stay, Charlton says. 

“Our tech team is considered a significant part of our business strategy, so there’s always an opportunity to work on exciting things that not only affect the company’s bottom line, but also impact how our fleet clients across North America run their businesses,” she says.

Cloud skills still integral to success

Because the cloud underpins most organizations’ digital initiatives, cloud architecture and multicloud management remain key roles — and difficult to fill. Here, as with cybersecurity, depth of experience is mission critical, says S&P’s Kocherlakota.

“With the rapid adoption of cloud technologies and companies all over the world undergoing digital transformation, the demand for skilled professionals has surged,” addsAvnet’s Chan. “There is intense competition among companies as various industries invest in these initiatives, and they are vying for the same limited pool of skilled professionals.”

The upside of recent tech layoffs is that there has been more cloud talent on the market this year. “We have seen the market open for some of our more difficult-to-fill cloud and product management roles,” says Lobo of Ensono. “For the last few years, candidates have had limitless options and salaries have been increasing significantly with the demand. The current economy has created disruption and growing companies can hire talent that may have been out of reach two years ago.”

Filling the gap: Approaches that work

Short of wishing for more tech layoffs, there are things that IT leaders can do to meet their needs in a tight tech talent marketplace. CIOs shared some of their best practices and advice:

Enlist non-IT resources. “Technology development is no longer exclusive to the IT team,” saysAvnet’s Chan, who has had success bringing business users into the IT fold to take on IT workloads. Chan has also leaned on low-code/no-code tools to help meet his app development and automation needs. “We can now leverage our non-IT teams to develop applications within the environment. Individuals with minimal coding knowledge can now create functional applications through visual interfaces, pre-built templates, and drag-and-drop functionalities,” Chan says.

Build the bench. Avnet also partners with universities and other organizations to offer internships and junior placement opportunities. “This allows us to train young talent to take on the work in areas where there is a big need for a skilled workforce,” Chan says.

Grow your own. IT leaders are increasingly investing in skills development to bridge gaps from within. To do so, “companies need to project their demand ahead of time and train and develop an entry-level pool for the desired skillsets they require,” says Khan of Everest Group. 

At Ensono, Lobo has created academies for technical domains such as mainframe computing and cloud, enrolling students based on forecasted needs. Similarly, S&P has built an internal tech accelerator program called EssentialTECH. “We’ve created opportunities for our people to learn, grow, and apply skills in a dynamic technology environment and support the future of work,” Kocherlakota says, adding that this effort is particularly important in nascent areas like generative AI. “Companies that have invested in talent management and development when it comes to AI and large language models will leap over others who may have not focused here.”.

For specialized skills, internal development is critical, agrees Jen Raimer, director of talent management at Merchants Fleet, which offers an assortment of tools, resources, and professional certifications. “Upskilling and reskilling simultaneously support the growth of your employees’ careers and the growth of the business,” Raimer says. 

Work closely with HR. Speed is vital in a tight talent market. “It all starts by partnering closely with our talent acquisition team to make sure we’re aligned on staffing needs and follow a defined process,” says Fleetcor’s duFour. “This allows us to move quickly in identifying and pursuing candidates before they’re scooped up by someone else.”

Build your brand. With upward pressure on compensation, CIOs must offer a compelling employee experience to compete with higher-paying alternatives. “Rather than engaging in bidding wars to attract talent, differentiate your company from competitors,” advises duFour. Skills development, clear career paths, a culture of diversity and inclusion, and the ability to make an impact are all potential selling points.

To broaden his IT marketing efforts, duFour leverages his leadership team as subject matter experts in the media. “I’ve had numerous senior-level candidates reference articles, podcasts, or panels featuring me or others on our IT staff during the interview process,” duFour says. Merchants Fleet also gets creative in marketing its tech roles. “We try to infuse a little bit of our company’s personality into our marketing efforts, to give people a taste of the fun and welcoming environment they’ll be stepping into,” says Raimer. “We understand that tech candidates are likely fielding multiple offers, so we take every opportunity to stand out.”

Rethink job descriptions. Focusing on what’s essential. “The more unique skill sets we layer into the requirements and the more prescriptive we are in the background we’re targeting the more difficult the search,” says Ensono’s Lobo. “Think about what skill sets are really needed to be successful in the role and what can be trained.” Tools like LinkedIn Insights can offer a look at what’s available in the market to help hone the search.

Invest in the interview. The experience a candidate has during the interview process can be a make-or-break one. “It really sets the tone,” says Raimer. “Some of the creative things we’ve done include inviting candidates to join innovation sessions, staff meetings and company events for a ‘look behind the curtain.’” 

IT leaders and hiring managers should be willing to flex their approach as needed. “Don’t be afraid to pull out the stops and get creative when you find a candidate that you’re really excited about,” Raimer advises. “We constantly ask ourselves, ‘What will it take to attract and retain this candidate?’ It’s important to meet people where they are in their career journeys, and you need to be open to tailoring or personalizing the hiring experience in order to create meaningful connections.”

Use contractors and partners strategically. Chan leverages strategic partners to address acute needs as he develops internal talent. CIOs can also “explore innovative approaches to talent — such as experimenting with workers who are part of the gig economy,” he adds. “This allows businesses to tap into a vast pool of talent, access specialized skills, and increase flexibility while effectively managing costs.”

Chan also utilizes IT partners to handle lower-value work so he can move his own IT pros up the value chain. He gives employees in IT operations the chance to shift to strategic delivery, solution design, business consultancy, and innovation, handing over operations tasks to managed services partners.

Accuro’s Isaac, who has struggled to find UI designers and programmers,also advises using staffing services and temp-to-hire to “test drive” candidates. “There’s a little higher upfront cost,” Isaac says, “but it’s much better than making a long-term hiring mistake.”