Workplace

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.

Workplace

You need a healthy ‘debate culture’

From their first day, employees at Appian are encouraged to disagree with anyone at the company — including the CEO. Here’s how it works.

Appian co-founder and CEO Matt Calkins wants his employees to disagree with him.

Photo: Appian

Matt Calkins often hears that he’s polite, even deferential. But as CEO of Appian, he tells employees to challenge each other — especially their bosses — early and often.

“I love arguments. I love ideas clashing,” Calkins said. “I regard it as a personal compliment when someone respectfully dissents.”

Keep Reading Show less
Allison Levitsky
Allison Levitsky is a reporter at Protocol covering workplace issues in tech. She previously covered big tech companies and the tech workforce for the Silicon Valley Business Journal. Allison grew up in the Bay Area and graduated from UC Berkeley.

Some of the most astounding tech-enabled advances of the next decade, from cutting-edge medical research to urban traffic control and factory floor optimization, will be enabled by a device often smaller than a thumbnail: the memory chip.

While vast amounts of data are created, stored and processed every moment — by some estimates, 2.5 quintillion bytes daily — the insights in that code are unlocked by the memory chips that hold it and transfer it. “Memory will propel the next 10 years into the most transformative years in human history,” said Sanjay Mehrotra, president and CEO of Micron Technology.

Keep Reading Show less
James Daly
James Daly has a deep knowledge of creating brand voice identity, including understanding various audiences and targeting messaging accordingly. He enjoys commissioning, editing, writing, and business development, particularly in launching new ventures and building passionate audiences. Daly has led teams large and small to multiple awards and quantifiable success through a strategy built on teamwork, passion, fact-checking, intelligence, analytics, and audience growth while meeting budget goals and production deadlines in fast-paced environments. Daly is the Editorial Director of 2030 Media and a contributor at Wired.

Gopuff says it will make it through the fast-delivery slump

Maria Renz on her new role, the state of fast delivery and Gopuff’s goals for the coming year.

Gopuff has raised $4 billion at a $15 billion valuation.

Photo: Gopuff

The fast-delivery boom sent startups soaring during the pandemic, only for them to come crashing down in recent months. But Maria Renz said Gopuff is prepared to get through the slump.

“Gopuff is really well-positioned to weather through those challenges that we expect in the next year or so,” Renz told Protocol. “We're first party, we control elements of our mix, like price, very directly. And again, we have nine years of experience.”

Keep Reading Show less
Sarah Roach

Sarah (Sarahroach_) writes for Source Code at Protocol. She's a recent graduate of The George Washington University, where she studied journalism and criminal justice. She served for two years as editor-in-chief of GW's independent newspaper, The GW Hatchet. Sarah is based in New York, and can be reached at sroach@protocol.com

Enterprise

AT&T CTO: Challenges of the cloud transition are interpersonal

Jeremy Legg sat down with Protocol to discuss the race to 5G, the challenges of the cloud transition and nabbing tech talent.

AT&T CTO Jeremy Legg spoke with Protocol about the company's cloud transition and more.

Photo: AT&T

Jeremy Legg is two months into his role as CTO of AT&T, and he has been tasked with a big mandate: transforming the company into a software-driven business, with 5G and fiber as core growth areas.

This isn’t Legg’s first CTO gig, just his biggest one. He’s an entertainment biz guy who’s now at the center of the much bigger, albeit less glamorous, telecom business. Prior to joining AT&T in 2020, Legg was the CTO of WarnerMedia, where he was the technical architect behind HBO Max.

Keep Reading Show less
Michelle Ma

Michelle Ma (@himichellema) is a reporter at Protocol, where she writes about management, leadership and workplace issues in tech. Previously, she was a news editor of live journalism and special coverage for The Wall Street Journal. Prior to that, she worked as a staff writer at Wirecutter. She can be reached at mma@protocol.com.

Workplace

How Canva uses Canva

Design tips and tricks from the ultimate Canva pros: Canva employees themselves.

Employees use Canva to build the internal weekly “Canvazine,” product vision decks, team swag and more.

Illustration: Christopher T. Fong/Protocol

Ever wondered how the companies behind your favorite tech use their own products? We’ve told you how Spotify uses Spotify, How Slack uses Slack and how Meta uses its workplace tools. We talked to Canva employees about the creative ways they use the design tool.

The thing about Canva is that it's ridiculously easy to use. Anyone, regardless of skill level, can open up the app and produce a visually appealing presentation, infographic or video. The 10-year-old company has become synonymous with DIY design, serving as the preferred Instagram infographic app for the social justice “girlies.” Still, the app has plenty of overlooked features that Canvanauts (Canva’s word for its employees) use every day.

Keep Reading Show less
Lizzy Lawrence

Lizzy Lawrence ( @LizzyLaw_) is a reporter at Protocol, covering tools and productivity in the workplace. She's a recent graduate of the University of Michigan, where she studied sociology and international studies. She served as editor in chief of The Michigan Daily, her school's independent newspaper. She's based in D.C., and can be reached at llawrence@protocol.com.

Latest Stories
Bulletins