Upskilling and reskilling

Looking to Engage and Upskill Your Tech Workers? Follow This Company’s Lead

Illustration of tech worker working at their desk.

When Liz Anderson, director of solutions delivery at Ryder System, wanted to upskill this past year to meet her OKRs (objectives and key results), she knew where to turn: #LearnWithRyder, the company’s IT learning program. 

As a leader, Liz wanted to communicate more clearly in her writing, so she took a LinkedIn Learning course, Thinking Creatively. She also wanted to identify any inefficiencies in her team, so she studied value-stream mapping through a #LearnWithRyder learning path on lean and agile thinking. 

“#LearnWithRyder has been extremely beneficial in taking my team to the next level,” Liz says, “and it’s strengthened my leadership by demonstrating that you don’t stop learning because you have X number years experience or X number years in the field.” 

Liz is one of the trucking and logistics company’s 560 full-time employees eligible for #LearnWithRyder, which was designed to support the company’s tech workers’ in their learning.

The program is unique in a few ways. For starters, #LearnWithRyder was positioned as a high-priority, strategic initiative. It’s about more than a new learning platform. And it relies heavily on change management techniques to motivate people to learn. 

It’s also been wildly successful. 


Let’s take a look at what the company did and how they did it: 

1. Be intentional about what you want to achieve

From the very start, Ryder’s chief information officer Rajeev Ravindran and vice president of transformation Luis Zayas sent the message that learning was critical to the company’s strategy. And Ryder’s Eliza Fendell and Lex Schroeder, who oversee #LearnWithRyder as part of their roles in the transformation and change enablement team, knew that they wanted to align learning to business goals

This included three business objectives:

  • The company wanted to close some skills gaps and bring employees up-to-speed.
  • The company wanted to boost retention in IT — even though Ryder employees tend to stay at the company a long time. 
  • Ryder wanted to attract the best new tech talent available. 

 “We were very clear about what we were trying to achieve,” says Eliza, Ryder IT’s director of change enablement, “and we needed a high-performance learning culture to deliver on our strategy.”

2. Get senior leaders and other team members on board

One of the first tasks for Eliza and Lex, the senior manager of technology transformation enablement, was to interview senior leaders. This included deeper conversations with Rajeev and Luis and all the VPs, about where the team needed to upskill and develop new capabilities. “We tried to be really intentional about starting at the top,” Lex says, “beginning with listening to the VPs.”

The change enablement team asked leaders what they thought employees needed to learn — and were surprised by what they heard. Yes, the VPs wanted Ryder’s techies to upskill on everything from cybersecurity to Microsoft Azure. “But the first thing all of them said, which was just cool and a bit surprising to me,” Lex says, “was that they wanted more emotional intelligence, things like navigating complexity, giving feedback, and collaborating.”

Leaders were particularly interested in helping their tech employees become, Lex says, “more mindful and aware of how they communicated.” 

3. Ask the L&D team for help

Because Eliza was a learning expert — but no one else on the team was — they turned to Ryder’s enterprise learning and development team for help. 

Although IT already had a learning platform, employees didn’t use it much. The change enablement team explained to L&D that they wanted a new learning platform that could provide training in both soft and hard skills. But they also wanted to work with someone who could be a true partner and help them think about how to keep employees’ skills fresh. The L&D team suggested LinkedIn Learning. 

The change enablement team connected with Maryann Angelella, a LinkedIn account director, and found the collaborator they were after. They launched #LearnWithRyder — with Linkedin Learning — on May 1, 2023. 

4. Take a change management approach to learning

Because Eliza and her team were change management experts, they applied change management techniques to encourage employees to learn. “Ryder took the approach that they needed to change behaviors,” Maryann says. “They needed to change employees’ mindsets from ‘not learning much’ or ‘learning isn’t an everyday event’ to ‘learning as part of our normal workflow.’” 

How did the change enablement team do this? They started slowly and introduced new learning resources one step at a time to get people in the habit of learning, rather than focusing on what employees learned. “Using change management best practices,” Maryann says, “made them successful faster.” 

5. Communicate regularly to employees

As soon as #LearnWithRyder was launched, Lex started sending a biweekly newsletter to employees, encouraging them to learn. The newsletters touched on issues relevant to IT employees and always included links to courses, which ranged from Fundamentals of Sustainable Supply Chains to Managing Your Emotional Response to Workplace Stress

“Every time we sent out a communication, it was like, boom!” Eliza says. “Our LinkedIn Learning accounts would go through the roof because employees were purposely taking the courses we sent them.”

6. Gamify learning and encourage competition 

Once a quarter, Eliza’s team hosted an interactive meeting, which she describes as “this really cool thing you could log into and you’re in this virtual reality space, this kind of hangout zone.” After people spent time there, the change enablement team brought employees back (virtually) to an auditorium where the CIO, Rajeev, set direction for the team and reflected on his own learning. 

But they also made a game out of learning. During the meeting, the change enablement team awarded $20 Amazon or $10 Dunkin’ Donuts gift cards to employees who met certain goals, like being one of the first 15 people to take the How to Use LinkedIn Learning course or the first 15 to post on LinkedIn using the #LearnWithRyder hashtag. 

The change enablement team encouraged competition between departments too. In meetings with leaders, they highlighted the number of hours that the enterprise technology services team had logged, as compared with those in, say, supply chain and dedicated transportation solutions.

“Competition, we learned, is a healthy way to drive numbers up,” Eliza says. 

7. Make learning as accessible as possible

Because people are busy, the change enablement team tried to make #LearnWithRyder as accessible as possible. They encouraged employees to use the mobile LinkedIn Learning app. They made learning available through Microsoft Teams. And in their newsletters, they highlighted that leaders sometimes listened to courses while at the gym. 

For Sam Settle, Ryder’s senior director of technology delivery, this was a gift. Sam travels frequently for work and downloads courses, so he can watch them while waiting in airports. Because he wanted to become an even better manager, he watched a number of courses, including several on how to have difficult conversations. “Nobody,” he says, “likes to have difficult conversations, not even the person who’s starting them. But these courses were helpful and gave me more confidence in how I’m leading my team.” 

Final thoughts: The numbers speak for themselves

While the goal of #LearnWithRyder is to increase employees’ skills, the change enablement team focused their first-year efforts on building a learning culture and getting employees engaged. During the second year, they’ll work on closing skills gaps

Still, Ryder IT hit its first-year goals right on. #LearnWithRyder had a 95% activation rate, compared to a 48% rate among their LinkedIn Learning peers. Nearly three-fifths (59%) of #LearnWithRyder participants became repeat users, compared with the peer median of 49%. And their login rate was 50% higher than peers in their industry, according to LinkedIn Learning data. 

“Everything we did was intentional,” Eliza says. “We had a plan, and we experimented with what worked and what didn’t work. And we kept doing the stuff that worked.” 

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