As the IT landscape accelerates toward a more automated, AI‑driven future, the workforce powering that transformation is evolving just as quickly. In 2026, success for IT service providers (ITSPs) and SMBs will hinge not only on adopting new technologies, but on building, developing and retaining the talent capable of leveraging them. From smarter hiring strategies to the rise of AI‑empowered entrepreneurs, GTIA members predict a year defined by skills growth, accountability and a renewed focus on people. Here are 10 key workforce trends shaping the year ahead.
SMBs Will Spend on Tech, But Expect Results
“Technology spending will stay strong as small and medium-sized businesses continue to see technology as a key differentiator. Implementation will be the challenge, getting results from the investment, not just a shiny new LLM. That need will continue to feed the ITSP market. It will be a 'write-your-own-check' year for ITSPs who focus on delivering business-focused solutions, and it will be harder than ever for those focused only on technical ‘janitorial’ work.”
– Joe Rojas, founder, Start Grow Manage
Upskilling Workforce Becomes Higher Priority
“As tech modernization accelerates, organizations are realizing that the real challenge isn’t the technology itself, it’s having the right talent in place. In 2026, I predict that workforce upskilling will become a top priority as companies invest in training programs to keep employees equipped for modern architectures, automation tools and cloud environments. This focus on continuous learning will be critical for companies looking to maintain productivity and stay competitive as technology evolves.”
– Amy Kincaid, market director, Robert Half
AI, Automation Make Filling High-Level Roles Even More Important
“ITSPs and channel companies that do not fully embrace becoming talent factories will struggle to fill key high-level roles. This has been an issue for years, but the problem will increase as reliance on automation and AI accelerates. It’s actually easier to develop an employee into a unicorn than it is to find one on the open market. Hire smart, hard working culture fits early in their career, retain them, and develop their skills!”
– Dave Cava, owner, PeopleSharp
Hiring the Right Person vs. the First Person Will Be a Differentiator
“In 2026, the IT teams that thrive won’t just be the ones hiring the quickest. They’ll be the ones whose HR partners are thoughtfully building the right mix of people and skills. Instead of focusing only on job titles, they’ll look at what teams can actually do and bring together full-time staff, contractors and fractional experts in a way that feels flexible and smart. They’ll treat AI as a tool that helps people grow, not one that replaces them. And as remote work continues to spread, HR partners will design work that’s safe, compliant and supportive, creating teams that are healthier, stronger and ready for the inevitable chaos that comes with running an IT business.”
– Tiffany Bell, founder and HR business partner, Empower People Ops
AI Capabilities Will Create More Entrepreneurs
“In 2026, I believe people will truly begin to recognize how AI can help them work faster, think better and solve problems more efficiently. Those who invest in themselves and learn to use technology as a personal advantage will get ahead—expanding their skill sets and gaining the confidence to support themselves in new ways. This shift may even move some individuals out of traditional jobs as they launch their own lifestyle businesses. As more people experiment with AI-driven capabilities, we’ll see a rise in entrepreneurs and a wave of new products designed to solve problems we don’t even recognize yet. Some of these ventures will succeed and others will fail, but the common thread will be the same: People using AI to ask, ‘How can I be better?’—and having the tools to act on the answer immediately.”
– Desraie Thomas, director of community, Lexful
IT Competency Shifts from Exploration to Accountability
“In 2026, the baseline for IT competency shifts from exploration to accountability. Because these tools are now universal, the demand for speed and the transparency of execution will skyrocket. We have effectively swapped the workforce’s hammer for a nail gun. Mastering this isn't just a bonus—it is the fundamental trade skill required to meet this new level of expectation. It’s no longer about who has the tool; it’s about who has the discipline to use it effectively.”
– Roy Watanabe, Director, IT Infrastructure & Operations, The Kennedy Collective
Workforce Reductions Won’t Have Big Impact on ITSPs
“Big tech companies will continue significant workforce reductions … and it still won’t matter for ITSPs. ITSPs are generally looking for people who have experience with SMB technology and multi-tenant software tools and routinely provide awesome customer service. Those people generally don’t come from Meta, Amazon or Verizon!”
– Dave Cava, owner, PeopleSharp
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