CTO to CEO: The case for putting the tech expert in charge

Parag Agrawal is one of the few tech industry CTOs to nab the top job. But the tides may be shifting.

Parag Agrawal

Parag Agrawal’s appointment to Twitter's CEO seat is already alerting a new generation of CTOs that the top job may not be so out of reach.

Photo: Twitter

Parag Agrawal’s ascension to CEO of Twitter is notable for a few reasons. For one, at 37, he’s now the youngest CEO of an S&P 500 company, beating out Mark Zuckerberg. For another, his path to the top as a CTO-turned-CEO is still relatively rare in the corporate world.

His leap suggests that CEO succession trends may be shifting, as technology increasingly takes the center stage in business and strategy decisions not just for tech companies, but for the business world more broadly.

In a 2019 survey of 194 technology officers, Korn Ferry found that 51% of CTOs wanted to be CEO at some point during their career, but only 12% said that was the role they wanted next.

Eric Singleton never wanted to be a CEO. As CTO of Strax Networks Inc., an AR distribution platform, he was comfortable “behind the scenes” and “reluctant” to take on the more public-facing role of CEO. Prior to co-founding the company, he had a long career as a CIO at Fortune 500 retail companies like Chico’s FAS and Tommy Hilfiger. But on the urging of his board, which includes former Turner President David Levy and Jeffrey Flug of Shake Shack, Singleton agreed to step into the top job.

CTOs are increasingly being groomed by corporate boards as part of their CEO succession planning, according to Ash Athawale, senior managing director for Robert Half’s executive search division. Athawale told Protocol that he’s witnessed an increase in attention towards technology leaders as potential future chief executives.

The reason? Tech is now central to core business functions across all industries, said Singleton. Whether it’s manufacturing on the shop floor or navigating supply chain issues, talking to the tech lead is no longer an “afterthought” for business leaders, he told Protocol. For tech companies in particular, where the basis of the product is tech itself, the increased importance of the CTO is “a natural evolution.”

Among the big tech companies, however, Agrawal is still a rarity: a CTO who shot straight to the top. Amazon CEO Andy Jassy started as a marketing manager at Amazon and helmed AWS before taking over from Bezos. Satya Nadella also led the cloud and enterprise group at Microsoft before he was appointed CEO. Tim Cook, like many CEOs, was chief operating officer until he took over the CEO reins at Apple.

You can count on one hand the number of big tech industry CTOs who became CEOs. Pat Gelsinger did so at Intel, but only after a brief stint as CEO of VMware. Of direct CTO to CEO ascendants, the most notable are Verizon CEO Hans Vestberg and former Etsy CTO Chad Dickerson, who became CEO in 2011 and led the company through its IPO until 2017. Bryan Dove was also CTO at Skyscanner before his reign as CEO from 2018 to 2020.

NEW YORK, NY - MAY 12: Chad Dickerson, CEO, Etsy speaks onstage at the WIRED Business Conference 2015 at Museum of Jewish Heritage on May 12, 2015 in New York City. (Photo by Stephen Lovekin/Getty Images for WIRED) Etsy CEO Chad Dickerson Photo: Stephen Lovekin/Getty Images for WIRED

Part of the reason it’s so rare for CTOs to become CEOs is that the skill sets are in some ways radically different. The CTO job is often “more siloed than anything else” in the C-suite, according to Athawale. They might be helping the sales team, but they’re not responsible for sales typically. They might know what needs to be marketed, but they’re usually not marketing to anybody themselves. That’s why, historically, CEOs often came from the sales or operations side of things.

Despite all this, Agrawal’s appointment to the CEO seat is already alerting a new generation of CTOs that the top job may not be so out of reach. Since the announcement on Monday, Athawale has already heard from a number of technology leaders asking him, “How did that happen? Can I also be a CEO?”

Singleton has advice for other CTOs who have their eye on the chief executive seat: Hone your financial skills, challenge your perceived level of business acumen and brush up on your legal education with the chief counsel. “No matter how great you are on the tech side, that’s not an automatic translation to being a terrific leader,” he said.

Experts in the executive talent space also agree that the key to nabbing a top job is simple: Get your hands on some P&L experience. Even if it’s at a small level, ownership of a business unit shows the board that you have the financial acumen and skills necessary to turn a profit and lead the business.

Although CTOs usually have P&L experience, they don’t always have experience managing P&Ls across multiple divisions, said Joel Beasley, host of the Modern CTO podcast. And while Agrawal and other CTOs like him might have the skills to successfully evaluate and hire tech talent, they also might not have the same acumen for, say, evaluating a potential finance or marketing hire. Those are skills that can only come with experience.

At the end of the day, early planning is critical for successful CEO transitions. Corporate boards need to make sure that they start preparing potential CEO successors early, at least 12 to 24 months in advance of a CEO departure, recommended Athawale. If that person is a technology leader but doesn't have finance or operations experience, work with them to develop those skills.

One notable exception to the CTO to CEO narrative? Oracle’s Larry Ellison, who bucked the trend and went the other direction, stepping down as CEO to become CTO in 2014. He’s still executive chairman of the company, of which he owns an approximately 35% stake, making him in some ways current CEO Safra Catz’s de-facto boss.


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