Upskilling Your Employees for Retention with Richard Doran

Upskilling Your Employees: The New Retention Strategy

A Leadership Briefing with Richard Doran, Founder & President of Sierra ITS

How do you retain your best employees in an era of rapid technological change? According to Richard Doran, Founder and President of Sierra ITS, the answer lies in one powerful idea: learning is the new loyalty.

In a recent Leadership Briefing hosted by Alex Jarett, Richard shared how upskilling has become one of the most effective ways to retain talent, build resilience, and create a culture that keeps great employees engaged — especially as organizations adapt to AI and digital transformation.

The Shift from Technical Skills to People Development

Richard has seen a major change in what it takes to lead successful technology organizations. As he puts it, “Upskilling is how companies prove they value potential as much as performance.”

Companies that invest in developing their employees signal that they’re not just focused on short-term results — they’re building long-term capability. When employees see a path forward and understand that their organization is invested in their growth, they stop looking elsewhere.

“When people see a path forward, they stop searching for opportunity elsewhere because they can get the value by working with people they know, like, and trust.” — Richard Doran

Learning Is the New Loyalty

In this discussion, Richard emphasized that continuous learning isn’t just a perk — it’s a retention strategy.

“Learning is the new loyalty,” he said. “Employees stay where they grow.”

Upskilling helps organizations build a workforce that’s adaptable, resilient, and future-ready. It also ensures that institutional knowledge — the deep understanding of culture, processes, and systems — stays within the company rather than walking out the door.

Replacing experienced employees is expensive, and new hires often take months to learn the culture, the tech stack, and the business goals. By helping existing employees grow into new roles, companies not only avoid turnover but increase engagement and productivity.

Building a Culture of Growth

Richard also highlighted the role of culture in upskilling success. Organizations that embed learning into their culture — through mentorship, stretch projects, and visible career mobility — are the ones that thrive.

“When upskilling isn’t baked into the culture,” he said, “there’s a lack of mentorship, a lack of career mobility, and companies end up languishing in mediocrity.”

He pointed out that in today’s remote and hybrid environments, companies need to be even more intentional about maintaining these connections and providing opportunities for employees to grow together.

A Real-World Example: Turning Turnover into Retention

Richard shared a story of a mid-sized manufacturing firm that faced high turnover despite raising salaries to match competitors. The real issue wasn’t compensation — it was growth.

After launching an internal AI and data literacy program, employees began to advance into new roles:

• Analysts became data engineers.
  
  
• Project coordinators moved up to project managers.
  
  
• Technologists advanced into leadership positions.
  
  

The results were immediate: productivity increased, retention soared, and the company built a more motivated, future-ready team.

Frameworks That Work

While Sierra ITS has a clear framework for helping companies design and implement upskilling programs, Richard explained that every organization is different. The key is customizing the approach to the company’s needs, workforce, and culture.

“Each organization has different inputs,” he said. “We fine-tune our approach based on the organization — but there’s always a solution.”

Learn More

As Richard summed it up, upskilling isn’t just about skill gaps — it’s about building loyalty through learning and keeping the best people growing inside your organization.

📩 To learn more or explore how to start your own upskilling and retention initiative, connect with Richard Doran at Sierra ITS. 

This Leadership Briefing was hosted by Alex Jarett, Founder of the Technology Executives Club, The AI Thought Leadership Platform for Technology Leaders, Tech Founders and B2B Executives