By Ryan M. Sutton, executive director, Technology, Robert Half
Technology modernization isn't just another item on the corporate agenda—it’s a necessary and often complex initiative that supports almost all other tech priorities for 2026. IT leaders are primarily focused on security, AI and data initiatives this year, according to research for Robert Half’s 2026 Tech Priorities and Opportunities report. And they need modern infrastructure to protect, innovate and deliver results for the business.
But modernizing technology comes with challenges. Many organizations have accumulated technical debt that requires significant resources and investment to improve or replace the outdated or suboptimal technology. Robert Half’s research also reveals that hiring professionals with the required capabilities for modernization projects and closing skills gaps in existing staff are critical obstacles for IT leaders.
The stakes are high: unfilled positions and a lack of skilled professionals can lead to delayed projects, increased employee burnout and ultimately, lost revenue. For many organizations, coming up with a technology modernization strategy, including a talent plan, is no longer optional. It’s become a driver of growth, efficiency and AI adoption.
Technology modernization: How to build teams for AI and data transformation
Why a tech modernization strategy matters in 2026
How can you achieve your technology modernization goals?
Start by understanding what IT modernization means for your organization. It's more than swapping out old systems; it's about rethinking more precisely what you want it to do while keeping an eye on the future. Our survey of IT leaders reveals where many teams are focusing their tech modernization efforts. There’s no surprise that AI integration projects top the list, as AI adoption and investments continue to grow across organizations.
Top tech modernization initiatives for 2026
- AI-driven automation, agentic and generative integration (53%)
- Cloud migration or transformation (51%)
- Cybersecurity upgrades (48%)
- Data architecture improvements (45%)
Source: Robert Half survey of more than 350 technology leaders in the U.S.
But the pressure to both tackle these modernization initiatives and keep core systems and services running—all with limited resources—can lead to costly delays and compromises in project success. Balancing both short-term gains and long-term scalability and sustainability is very important when planning tech modernization projects, and having a clear vision helps you build the business case and get leadership buy-in for the resources you need. A strong technology modernization strategy typically includes prioritizing high-impact systems, aligning modernization with business goals and building teams with the right mix of technical and business expertise.
Tech hiring insights for 2026
Explore tech hiring insights
Explore research by company size and strategies to help you align the specialized talent needed for today’s tech priorities.
Critical roles and skills for a successful technology modernization strategy
Let's look at what an effective technology team needs to see success with modernization projects. Robert Half's research for the 2026 Tech Priorities and Opportunities report reveals the scope of the challenge, with 45% of technology leaders say hiring talent with specialized technical skills is one of their biggest obstacles, while 42% report closing skills gaps in their departments.
Some skill areas prove particularly hard to staff. AI and machine learning skills are the hardest to find, cited by 45% of leaders, while IT operations and infrastructure support follow at 36%. Cloud architecture and operations and data engineering and analytics are also among the top skills gaps reported—and essential for many tech modernization efforts.
However, successful IT modernization requires more than technical expertise. Look for professionals who bring three essential capabilities: the strategic vision to modernize systems and map complex workflows, the business analysis skills to translate technical concepts across departments, and proven experience building scalable, sustainable solutions.
This combination of skills shows up in several key roles. Network and cloud engineers, software engineers, and IT project managers top the list of in-demand positions. These professionals can bridge the critical gap between legacy systems and modern solutions. DevOps engineers could also be vital to a technology modernization strategy, especially as organizations invest in initiatives like CI/CD enhancements, AIOps and MLOps.
See how organizations are strengthening their tech and IT skills bench to close gaps and deliver on 2026 priorities.
How to overcome technology modernization hiring challenges
Amid a competitive hiring environment, you need a strategic approach to securing talent. Here’s what works:
Look beyond job titles
When hiring for technology modernization projects, zero in on relevant capabilities rather than years of experience or exact title matches. Remember: the technical skills you need today might not have existed a few years ago. For example, a candidate might not have "AI governance" in their job history, but their experience in data ethics could make them ideal for your AI initiatives. Similarly, someone with strong business analysis skills might be perfect for tackling technical debt across departments, even if they haven't held that exact role before.
The interview is a great place to get a better sense of candidates’ capabilities and previous experience that may translate well to your open position. It also provides an opportunity to learn more about in-demand or emerging skills they present on their resume. For example, if AI and machine learning skills are featured in their application materials, consider asking for more details to better understand the scope of their experience, as using generative AI applications to support everyday work is different than building a generative AI model or integrating AI into an existing product or system.
As more candidates use AI to tailor application materials, hiring managers may need to dig deeper to understand the depth of their technical skills and experience.
Rightsize your hiring strategy
Hiring plans vary significantly by organization size. Understanding where you sit in the market and the latest hiring trends helps you set realistic expectations and competitive offers.
If you're a small business competing with larger organizations, focus on your unique advantages. Your technology modernization projects might offer candidates more direct impact and broader responsibility. You might also provide more flexibility in how work gets done or offer faster paths to leadership roles in the modernization effort. Larger organizations can attract talent with comprehensive benefits packages, established career development programs and the resources to take on the most ambitious modernization projects.
Embrace a flexible talent model
Adopting a flexible staffing approach that combines permanent employees and contract professionals, as well as consultants and outsourcing, to meet your organization’s specific needs can be a boon to successful technology modernization. Your permanent staff provides the foundation and continuity essential for long-term modernization initiatives. Contract professionals complement these teams by bringing specialized expertise for specific project phases or technical challenges. Working with a talent solutions firm like Robert Half can help you find candidates with the skills you need most and also align with your organizational culture and salary budget.
72% of tech leaders say they work with staffing firms to access specialized skills for complex projects, while 61% seek help with urgent or time-sensitive projects and 57% for large-scale transformation initiatives.
Many teams today are short on skill sets that are crucial for not only everyday IT operations but also for more complex initiatives such as tech modernization. Leaders must close skills gaps and build next-generation teams to reduce technical debt, modernize IT operations and drive digital transformation.
Need help building your tech team for 2026 priorities?
Hire tech talent
Robert Half can help you find skilled professionals to support technology modernization initiatives, from AI and security to cloud and DevOps.
