• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military

2

'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032

3

Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon

1

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military

2

'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032

3

Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon
C-SuiteNext to Lead

The CEO question that stumped a room full of COOs

By
Ruth Umoh
Ruth Umoh
Editor, Next to Lead
Down Arrow Button Icon
By
Ruth Umoh
Ruth Umoh
Editor, Next to Lead
Down Arrow Button Icon
June 8, 2026, 7:53 AM ET
dw
Freshworks CEO Dennis Woodside at the Fortune COO Summit in Scottsdale, Arizona, on June 2, 2026.Kristy Walker/Fortune

One of the more striking moments at this year’s Fortune COO Summit came when Dennis Woodside, the CEO of Freshworks and a former COO of Dropbox, asked the room a simple question: Who wants to be a CEO?

Recommended Video

Not many hands went up.

Woodside found that surprising. His view, he told the crowd, is that if you hold the COO title, it’s usually because your CEO and board already see you as potential CEO material, even if no one has said it out loud.

“If you have the title of COO, you have it for a reason,” he told the audience. “The board and your CEO decided that you are on a path to being ready, potentially to be the CEO.”

That observation resonated with me because, over the years of interviewing chief operating officers, I’ve often encountered the same hesitation. Many COOs are reluctant to say publicly that they want the top job, even when their careers suggest they are being groomed for it. Some genuinely prefer the operator role. Others seem wary of appearing overly ambitious.

But Woodside argues that leaders should be honest with themselves about whether they aspire to the CEO seat—and, if they do, communicate that ambition early.

Woodside speaks from experience. His unconventional career has taken him from M&A law and consulting to leadership roles at Google, Motorola Mobility, Dropbox, Impossible Foods, and now Freshworks. Along the way, he says, nobody explicitly told him that becoming COO often means being considered for the CEO pipeline. He had to figure it out himself.

His advice is straightforward: Master the job you have today, but don’t be afraid to tell your board and mentors where you want to go. “You have to have that conversation: ‘I want to be the CEO someday. Help me get there,’” he says.

In a business environment increasingly shaped by AI disruption, succession challenges, and leadership turnover, it’s a reminder that the COO role is often more than an operational assignment. It may be the clearest signal a company can send that it believes someone is capable of running the entire enterprise.

READ MORE: These COOs became CEOs. Here’s what they wish everyone knew about the tricky transition

Ruth Umoh
ruth.umoh@fortune.com

Smarter in seconds

FIFA fiefdom. How Gianni Infantino built a FIFA-dom with a tight grip on soccer’s biggest global event

Command center. ‘Stop building silos of excellence’: Peloton’s COO has a Navy playbook for the new era of supply chain chaos

Skills shift. The IBM executive tasked with retraining 30 million workers is changing how she thinks about the AI finish line

 

Leadership lesson

Walmart CEO John Furner on adaptability: “Getting comfortable with change in a world that continues to change, I think, is a really great trait for any leader.”

News to know

Trump urged Israel and Iran to stop firing after both breached the April ceasefire. WSJ

SpaceX’s amended IPO filing sets aside 5% of shares for select insiders and associates who can sell immediately after the IPO, bypassing the usual lockup period. Fortune

AI threatens blue-state jobs most, leaving Democrats especially vulnerable to a growing tech backlash. Fortune

U.S. Soccer is using AI to scout 70 million teenagers, a move its leadership says is reshaping how players are scouted and developed. Fortune

Just 12 Fortune 500 companies have endured more than two centuries of wars, economic crashes, and sweeping changes in American history. Fortune

Intel’s stock is up nearly 500% after CEO Lip-Bu Tan halved management layers, finally signaling a turnaround. Fortune

A sweeping AI and automation effort is helping Macy’s improve demand forecasting, speed deliveries, and personalize shopping. Fortune

American money has transformed soccer, but fans fear the profit chase is warping the game without fixing its finances. FT

Subscribe to Fortune Gulf Brief. Every Tuesday, this new newsletter delivers clear-eyed, authoritative intelligence on the deals, decisions, policies, and power shifts shaping one of the world’s most consequential regions, written for the people who need to act on it. Sign up here.
About the Author
By Ruth UmohEditor, Next to Lead
LinkedIn icon

Ruth Umoh is the Next to Lead editor at Fortune, covering the next generation of C-Suite leaders. She also authors Fortune’s Next to Lead newsletter.

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
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • 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
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in C-Suite

Man in a white shirt and jacket.
InnovationBrainstorm Tech
Marc Lore’s robots make 500 burrito bowls an hour. A human can make 45
By Amanda GerutJune 9, 2026
5 hours ago
AI isn’t replacing Hyatt’s salespeople—it’s freeing up a full day of work every week, according to the CEO
AIBrainstorm Tech
AI isn’t replacing Hyatt’s salespeople—it’s freeing up a full day of work every week, according to the CEO
By Sharon GoldmanJune 9, 2026
8 hours ago
The AI industry spent years chasing bigger models. Now it’s chasing efficiency
AIBrainstorm Tech
The AI industry spent years chasing bigger models. Now it’s chasing efficiency
By Sharon GoldmanJune 9, 2026
9 hours ago
Xbox CEO Asha Sharma speaks on stage at Fortune Brainstorm Tech 2026.
Big TechMicrosoft
‘Not an Allbirds Moment’: Xbox’s new CEO says she is grounding the console in gaming roots, not AI
By Sebastian HerreraJune 9, 2026
10 hours ago
BP’s new CEO Meg O’Neill rips up the energy giant’s playbook—and the ‘green’ era with it
EnergyBP
BP’s new CEO Meg O’Neill rips up the energy giant’s playbook—and the ‘green’ era with it
By Jordan BlumJune 9, 2026
10 hours ago
Three people having a seated discussion
AIBrainstorm Tech
‘Getting control where we can’: Europe wants sovereign AI, but most of the chips are from the U.S.
By Amanda GerutJune 9, 2026
11 hours ago

Most Popular

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
Asia
Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
By Kate O'Keeffe and BloombergJune 8, 2026
1 day ago
'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032
Economy
'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032
By Nick LichtenbergJune 9, 2026
12 hours ago
Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon
Environment
Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon
By Sasha RogelbergJune 8, 2026
1 day ago
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
Success
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
By Preston ForeJune 8, 2026
2 days ago
Current price of oil as of June 8, 2026
Personal Finance
Current price of oil as of June 8, 2026
By Joseph HostetlerJune 8, 2026
2 days ago
Gen Zers are arriving at college unable to even read a sentence—professors warn it could lead to a generation of anxious and lonely graduates
Success
Gen Zers are arriving at college unable to even read a sentence—professors warn it could lead to a generation of anxious and lonely graduates
By Preston ForeJune 7, 2026
3 days ago

© 2026 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.