• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
C-SuiteFortune 500 Companies

The CEO of $12 billion Ryder System caught a massive strategic blind spot after a simple question from someone in office supplies

Amanda Gerut
By
Amanda Gerut
Amanda Gerut
News Editor, West Coast
Down Arrow Button Icon
Amanda Gerut
By
Amanda Gerut
Amanda Gerut
News Editor, West Coast
Down Arrow Button Icon
November 28, 2025, 7:27 AM ET
Ryder System CEO and chairman Robert Sanchez
Ryder System CEO and chairman Robert Sanchez said a question from a board member unlocked a significant strategic insight. Courtesy Ryder System

The most dangerous words in business might be, “we’ve always done it this way,” and sometimes it takes an outsider to bring about change. 

Recommended Video

Ryder System CEO Robert Sanchez learned that early in his tenure in the top spot. Sanchez has been CEO of the transportation and supply chain management company since 2013, and when he got the job he brought with him two decades of experience in finance, technology, and operations. Five short months after being named CEO, he became board chair in May 2013.

As chair, Sanchez leads an annual strategy session with the other 10 directors on the corporate board, which has the power to hire and fire the CEO. The annual reviews are a chance for board members to run a post-mortem on the year prior, talk about the year to come, and preview the three-year strategic outlook so directors can kick the tires on Ryder’s plans. 

“It’s a great time for the board members to really pressure test our strategy and think about it in different ways,” said Sanchez, who previously served as the chief financial officer, chief operating officer and chief information officer at Ryder, which generated $12.6 billion in revenues last year. “We almost view it as an annual toll gate where we sit with them and say, ‘All right, here are the things that we told you we were going to do last year. Here’s what we got accomplished, and here are the new things we want to get done.’”

It was at an annual strategy session, Sanchez told Fortune, that one of the most illuminating moments emerged. Sanchez and the other senior executives were talking about market share in the truck leasing and rental business known as Fleet Management Solutions, while the board members listened. At the time, Ryder held 35% to 40% of the truck leasing market segment—nothing to sneeze at.

“We felt pretty good,” said Sanchez.

And then one board member from a completely different industry raised his hand to ask a question that would ultimately become a hugely pivotal moment for Sanchez and his team and Ryder. 

“Does that mean that 40% of the trucks that are on the road are from Ryder?” the director asked. 

“And I said, ‘Well, no, of course not,’” Sanchez recalled. “Then he goes, ‘Why is that? What do all the other truck owners do? Are they leasing from somebody else? Are they getting dedicated service from somebody else?’”

“No,” Sanchez told the director; other operators on the road probably buy their own trucks and have their own drivers. The director asked Sanchez point blank: “Why aren’t you guys going after them?”

“So, we all kind of stared at each other and said, ‘We’ll have to get back to you,’” Sanchez recounted. 

For context, the leasing market at the time was only 15% to 20% of all the trucks on the road. Meaning, 80% to 85% purchased and maintained their own trucks. So the big takeaway was really about why Ryder wasn’t going after that truck ownership market—the 80% to 85%. So for a full year afterward, Sanchez and his team strategized how to chip away at all the companies that don’t lease trucks from Ryder or any of its competitors, nor outsource transportation to them. 

“We realized that a large percentage of the market is do-it-yourselfers,” said Ryder. “So our strategy over the last probably 12 to 13 years has been chipping away at the do-it-yourself market when it comes to trucking and transportation.”

The independent director who asked the question? His background is in office supplies and has nothing to do with trucking. But he asked the question that crystallized a strategic insight that helped push more than a decade of execution. 

In hindsight, “it was pretty obvious,” said Sanchez. “But as a company that’s been around for 80 years, we really hadn’t looked at it that way.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
Amanda Gerut
By Amanda GerutNews Editor, West Coast

Amanda Gerut is the west coast editor at Fortune, overseeing publicly traded businesses, executive compensation, Securities and Exchange Commission regulations, and investigations.

See full bioRight Arrow Button Icon

Latest in C-Suite

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

Latest in C-Suite

sudhakar
CommentaryM&A
I’m the SolarWinds CEO. Here’s why a $4.4 billion move to go private was right for us
By Sudhakar RamakrishnaJanuary 8, 2026
17 hours ago
Jassy
Workplace CultureAmazon
Amazon demands proof of productivity from employees, asking for list of accomplishments
By Jake AngeloJanuary 8, 2026
18 hours ago
Mark DesJardine
CommentaryM&A
Warner Bros. Discovery’s board isn’t choosing a deal — it’s avoiding one
By Mark DesJardineJanuary 8, 2026
18 hours ago
The Diary of a CEO founder Steven Bartlett
SuccessThe Interview Playbook
Diary of a CEO founder says he hired someone with ‘zero’ work experience because she ‘thanked the security guard by name’ before the interview
By Emma BurleighJanuary 8, 2026
19 hours ago
A woman stands in front of a whiteboard speaking to a table of people.
Commentaryenterprise technology
AI isn’t failing your company. Your operating model is
By Katerin Le FolcalvezJanuary 8, 2026
20 hours ago
Future of WorkTech
The typical American plan to study for 22 years and work for 40 ‘is broken,’ VC CEO says. Thanks to AI, employees can’t coast after graduation anymore
By Marco Quiroz-GutierrezJanuary 7, 2026
2 days ago

Most Popular

placeholder alt text
Law
Amazon is cutting checks to millions of customers as part of a $2.5 billion FTC settlement. Here's who qualifies and how to get paid
By Sydney LakeJanuary 6, 2026
3 days ago
placeholder alt text
Success
Diary of a CEO founder says he hired someone with 'zero' work experience because she 'thanked the security guard by name' before the interview
By Emma BurleighJanuary 8, 2026
19 hours ago
placeholder alt text
Future of Work
AI layoffs are looking more and more like corporate fiction that's masking a darker reality, Oxford Economics suggests
By Nick LichtenbergJanuary 7, 2026
2 days ago
placeholder alt text
Workplace Culture
Amazon demands proof of productivity from employees, asking for list of accomplishments
By Jake AngeloJanuary 8, 2026
18 hours ago
placeholder alt text
Real Estate
Google billionaire Larry Page copies the Jeff Bezos playbook, buying a $173 million Miami compound that will save him millions in taxes
By Nick LichtenbergJanuary 8, 2026
16 hours ago
placeholder alt text
Future of Work
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
By Jake AngeloJanuary 6, 2026
3 days ago

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.