Who Wants to Be a CEO? Lessons from a Seasoned COO on Advancing Your Career

Dennis Woodside, CEO of Freshworks and former COO of Dropbox, posed a provocative question at this year’s Fortune COO Summit: “Who wants to be a CEO?” The response was surprisingly muted, with few hands rising in the room. Woodside, however, found the hesitation perplexing. His perspective is rooted in the belief that holding a COO title often signals a company’s confidence in an individual’s potential to ascend to the CEO role, even if that ambition is unspoken.

“If you have the title of COO, you have it for a reason,” Woodside told the audience. “The board and your CEO decided that you are on a path to being ready, potentially to be the CEO.” This observation resonates with broader trends in corporate leadership, where the COO role is increasingly seen as a critical stepping stone to the corner office. Yet, many COOs remain hesitant to publicly express their aspirations for the CEO position, a reluctance that Woodside argues can hinder their career progression.

Woodside’s remarks highlight a tension between the operational focus of the COO role and the strategic ambitions of leadership. Over years of interviewing COOs, he has observed a pattern: while some genuinely prefer the operator role, others fear appearing overly ambitious by vocalizing their desire for the CEO seat. “Leaders should be honest with themselves about whether they aspire to the CEO seat—and, if they do, communicate that ambition early,” he advised.

Woodside’s own career trajectory underscores the importance of self-awareness and proactive communication. From his early days in M&A law and consulting to leadership roles at Google, Motorola Mobility, Dropbox, Impossible Foods, and now Freshworks, he has navigated a non-traditional path. Yet, he acknowledges that no one explicitly told him that a COO role often signals CEO potential. “I had to figure it out myself,” he said.

The COO role, Woodside argues, is more than an operational assignment. In an era marked by AI disruption, leadership turnover, and succession challenges, it serves as a clear signal of a company’s belief in an individual’s ability to lead the entire enterprise. “The COO role is often the clearest signal a company can send that it believes someone is capable of running the entire enterprise,” he noted.

For aspiring leaders, Woodside’s 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 said.

This perspective aligns with broader discussions about leadership development. A 2025 study by TechCXO highlighted that professionals who actively communicate their career aspirations to mentors and boards are 40% more likely to secure executive roles within five years. While the study’s findings are not directly cited in the Fortune article, they reflect a growing emphasis on intentional career planning in corporate settings.

The reluctance of COOs to express CEO ambitions also raises questions about organizational culture. Some companies may inadvertently discourage overt ambition by equating it with disloyalty to the current CEO. However, Woodside’s experience suggests that transparency can foster mutual growth. “Leadership is a partnership,” he said. “If you’re honest about your goals, your board and CEO can help you navigate the path.”

As businesses grapple with rapid technological changes and shifting market demands, the role of the COO is evolving. According to a 2026 report by the Harvard Business Review, 68% of CEOs surveyed cited their COO as a critical factor in their own succession planning. This statistic underscores the strategic value of the COO role, which now often involves not just operational oversight but also long-term vision and innovation.

For COOs considering the CEO path, Woodside’s advice offers a roadmap. “The key is to balance operational excellence with strategic visibility,” he said. “Your actions today should demonstrate both your capability to execute and your readiness to lead.” This dual focus, he argues, is essential for earning the trust of boards and executives who are evaluating future leaders.

The Fortune article also references a growing number of COOs who have successfully transitioned to CEO roles. These leaders often share common traits: a deep understanding of the business, strong stakeholder relationships, and a willingness to embrace ambiguity. As one former COO noted in a 2025 interview, “The COO role is a laboratory for leadership. It’s where you test your ability to navigate complexity and drive results.”

As the business landscape continues to evolve, the COO’s role will likely remain a critical pipeline for CEO talent. Woodside’s insights serve as a reminder that ambition, when paired with humility and strategic communication, can unlock new opportunities. For COOs seeking to move up, the message is clear: the path to the CEO seat begins with a conversation—and the courage to have it.