How the top 3% of tech teams maximize upskilling ROI

How do you get the most out of your learning initiatives? Most organizations focus on general usage, measuring value by simple usage metrics. But we’ve found that how learners engage with learning content is a far more powerful driver of skill development and business value. 

To understand what separates high-performing learning and upskilling programs from the rest, our Value Realization team studied 556 of our “best-in-class” customers. These customers represent the top 3% of our B2B accounts by learning outcomes.

The findings are clear: frequency, personalization, and alignment to real-world work are the key to realizing greater value from learning.

Here’s what the best are doing—and how you can replicate it.

1. Frequent learning drives greater skills gains

It’s not how long you learn—it’s how often.

Our research found that users who engage with Pluralsight learning content seven or more days per month saw double the skill gain compared to those who binged content in a single long session.

Across our top-performing customers, this pattern held true consistently. Frequent learning touchpoints help cement knowledge, increase confidence, and encourage in-the-flow learning that gets applied more immediately.

How to encourage more frequent learning:

• Build learning into agile sprints of weekly standups

• Designate protected learning hours each week

• Encourage managers to discuss skill growth in one-on-ones
  
  

2. Personalized learning paths accelerate skill improvement

It’s old news: One-size-fits-all learning does not work. How you personalize learning is the big question. Pluralsight uses skill assessments through our Skill IQ feature to identify an individual’s skills gaps and then serve personalized learning recommendations.

Our research found that learners who followed those personalized learning paths tailored by Skill IQ improved their skill level by 72% in just 49 days. The most successful organizations had 87% of users enrolled in curated learning paths, and learning content aligned to 73% of individuals’ actual role responsibilities. This personalization meant that 90% of learners applied their new skills at the first opportunity!

How to personalize learning journeys:

• Use Skill IQ to identify role-based gaps

• Curate learning paths around real projects and initiatives

• Empower managers to co-own learning plans with their teams

3. Manager engagement and real-world use cases multiply value

The most successful best-in-class customers aligned their learning to specific initiatives and strategic outcomes. Those customers also partnered with Pluralsight’s customer success and Professional Services (ProServ) teams to ensure engagement in line with best practices, which included:

• Team managers accessing Pluralsight analytics 3+ times per month

• Protected learning time built into workstreams

• Equipping admins and people leaders to curate and track skill growth

Thanks to this intentional learning and partnership, learning became strategic, not just supplemental. As a result, these customers saw clearer ownership, stronger adoption, and more measurable impact.

How to engage management and apply real use cases to learning:

• Train team managers on using analytics during one-on-ones

• Align learning initiatives to org-wide transformations

• Reinforce early wins by showing progress within the first 30 days of kicking off a learning initiative
  

Conclusion

Many people see “best-in-class” and they think “big budget.” But what united these high-performing customers was not headcount or spend, it was how deliberately they approached learning. 

With the right structure and strategy, even lean teams can create an impactful, scalable upskilling engine that:

• Builds internal talent faster

• Improves productivity and work quality

• Reduces reliance on external hiring

Download our new Tech Upskilling Playbook to dig deeper into these practical strategies that will help you design a learning program that delivers real business results.