3 steps to capture ROI for L&D technology investments

In 2024, organizations spent more than $350 billion on cloud computing tech. And in 2025, 66% say they fund AI initiatives aggressively. Despite the high cost of investment, most organizations are still in the early stages of digital transformation, and skills gaps are impacting performance. 

In fact, IDC predicts that by 2026, more than 90% of organizations worldwide will feel the pain of the IT skills crisis, amounting to some $5.5 trillion in losses caused by product delays, impaired competitiveness, and loss of business.

With so much money on the line, how are organizations planning to overcome this challenge and see positive ROI? Upskilling with workforce development programs. 

Drew Firment, Pluralsight’s VP of Enterprise Strategy, explains how L&D leaders can get a seat at the table and ensure ROI from technology investments.

Watch the video for all of Drew’s insights.

Leading organizations develop and execute careful strategies for digital transformations like cloud migration and AI adoption. Organizations should take a similar approach to skill development.

This is where there’s a gap between leaders and laggards. Leading organizations invest in upskilling across the entire organization and determine what they have, where they want to go, and how they plan to get there.

“You’re really looking at it as a talent migration with the same methodical and comprehensive approach to your workforce development,” says Drew. “And that really requires these organizations to have a clear understanding of their current state in terms of their existing capabilities, what are their gaps, [along with] a very, very clear vision of their future state in terms of what are the roles and what are the underlying skills required.”

Once you gain those insights, you’ll have a clear path from your current state to your future state that engages and propels your organization forward.

Get upskilling tips from leading organizations.

Too often, L&D and tech leaders develop upskilling initiatives in silos. But without input from both teams, employees might not learn the right skills or have access to the right resources.

As an L&D leader, it can be hard to get a seat at the table with CIOs and CTOs to prove the value of learning investments for technology. Data is one way to get your foot in the door with executive decision makers. 

“Data-driven decisions are being used in technology to determine where those technology investments are going. In leading organizations, that same thing is being done with skill investments,” says Drew.

Here’s how you can help prove the ROI of learning investments and connect access to training to technology goals.

Only 33% of executives completely understand the skills their IT teams need, and 68% of technologists say leadership at their organization isn’t aware of the skills gaps in IT.

The first step is to determine your organization’s current state. Benchmark your team’s skill levels. What skills do your employees have? What skills don’t they have?

It’s important to use tools like Skill IQ rather than rely on self-evaluations. Our 2025 AI Skills Report found that 79% of executives and IT professionals fake their AI knowledge. There’s a number of reasons why employees may misrepresent their skills in either direction—benchmarking assessments provide a more objective look at skills across your organization. 

Just stress to your teams that these assessments aren’t tests. You won’t use their scores against them. They’re benchmarks, meant to help both of you determine where to focus skill development efforts.

Next, determine what you want to achieve with tech learning. What skills do your people need? What do you want tech roles to look like? Find the gap between where you are and where you want to be to guide your investment decisions. 

“That skills data really helps to inform leading organizations,” says Drew. “What’s your current state? What’s your progress? And then what are those investment needs in terms of skill development across your entire workforce?” 

Once you understand skills gaps across your organization, build personalized learning paths to fill them. At this stage, building momentum is key, and paths provide learners with a clear way forward. AI tools like Iris, Pluralsight’s AI Assistant, can help you create custom learning paths. 

Says Drew, “It’s really become a great way to accelerate the individual experience with a very personalized approach to learning. It understands your needs and can quickly go through our inventory of courses and content and be able to provide exactly what you need when you need it.”

Learn how to create custom learning paths for tech skills.

Pluralsight’s Developer Success Lab found that three factors contribute to ROI on learning: self-efficacy, a community of practice, and role-based belonging. 

In other words, learners are more likely to put their skills into action when they’re confident in their abilities, have access to a professional community for help and support while learning, and feel like they belong in their technical role.

Making sure your organization fosters a culture where this is possible will help you maintain upskilling momentum and long term positive ROI for your L&D investments. Creating hands-on learning opportunities can also help you tie skill development to business outcomes.

“Hands-on learning labs and sandbox environments allow the workforce to be able to put the paper into practice with these interactive multimodal learning opportunities,” says Drew. “And that is fundamentally important when you want to go from literacy to fluency and then, ultimately, apply it to your organizational outcomes.”

Learn more about the Developer Success Lab’s research.

Upskilling is key to getting return on investment from technology transformation. Taking a data-driven approach to tech learning investments can help you get a seat at the table with tech leaders, but supporting those investments with a learning culture is how you keep it.

Is your organization ready to drive ROI with AI? Use the AI Readiness Index to find out.