Blind spots block growth. Outreach gives you full visibility into what’s happening in your entire pipeline so you can coach better, forecast accurately, and close quicker. Streamline your revenue ops.
Serving as a CRO is hardly the beaten path to becoming a CEO. While sales leaders are relied upon to hunt for new business and spur growth, they are often overlooked when it comes to consideration for top dog.
A 2021 study from Spencer Stuart found that 85% of S&P 500 CEOs come from four positions: COO, CFO, divisional CEO, and candidates outside the C-suite. A 2023 McKinsey study found that only 11% of Fortune 100 companies even have a CRO.
However, this did not blunt Tom Pickett’s ascent. The current CEO of online mental health and wellness platform Headspace, former CRO of DoorDash, and veteran Google exec, has picked up a bag of tricks over the years. He spoke with Revenue Brew to discuss his journey from CRO to CEO, the “spectrum of the CRO,” and the advantages that come with running the show with a sales background.
(Being a former F/A-18 pilot and a “Top Gun” graduate from the Navy doesn’t hurt, either.)
Advantages of a CRO background
Pickett’s sales and growth experience was good training ground to learn about customer tendencies, and he’s used that knowledge to make decisions at Headspace.
“Coming from the commercial side of the business, you have this market orientation. You are on the tip of the sword in terms of understanding what the market need is, and you’re talking to customers on a daily basis,” Pickett said.
The ability to understand customers, as well as growth, was important to Headspace as it conducted its CEO search in 2024. According to Sean Brecker, CFO of Oura and a board member at Headspace, “Tom’s career stood out. His ability to scale technology-driven companies across B2B and D2C models, combined with his leadership in customer trust, safety, and policy, reflects the multifaceted strengths increasingly required of today’s CROs stepping into CEO roles.”
Different mindset needed for the CEO role
Four and a half years as DoorDash’s CRO and a decade at Google taught Pickett how to translate product into market value, how to work cross-functionally with other departments, and how to have an execution mindset. These skills served as the foundation for his CEO vision, and he likened the matriculation from CRO to CEO as similar to shifting from being a player to a coach.
“As a CRO, you are part of that process and an input to that process, but ultimately the job of the CEO is to set the strategy then create the conditions on the field so that your team can execute that strategy,” he said.
He added a truism: Your background before becoming CEO will dictate how the company is run.
Staying put versus finding new challenges
Some CEOs work their way up from the bottom, like Nike’s Elliott Hill, who started as a company intern in 1988. Others, like Pickett, pick up experience at several places before stepping into the CEO role.
Pickett was busy proving himself during his time at Google, working his way up the YouTube ladder, but ultimately knew that tech companies would have a bias toward product-oriented leaders.
“Google, being a technology-driven organization, if you don’t come from the tech side, it’s not going to happen,” Pickett said, “It was a little more clear to me that if I wanted to [be a CEO], I had to go jump to something else.”
The CRO spectrum
According to Pickett, there are different types of CROs: You’ve got your sales-type CRO who comes from a lead generation background, and on the other end of the spectrum, you’ve got your general management CRO who looks to expand responsibilities and knowledge across teams.At DoorDash, even as CRO, Pickett also oversaw the merchant side of its business. This meant a lot of control over the product roadmap, over the sales and customer success organization, but really understanding—and driving—the P&L of that segment. As the revenue leader, he got to play in all parts of the business, not just in sales. “I know there’s a spectrum in terms of CEO and CRO responsibilities, but I think the more general management [skillset you have], then the more likely you’re going to be a better fit for the CEO job,” he said.
This is what Julia Cheek, CEO of Every Health and a Headspace board member, said Headspace was looking for when hiring Pickett.
“Tom is widely respected for his transparent and authentic leadership style, strong personal accountability, and leading by example,” Cheek wrote in an email to Revenue Brew.
Pickett stressed adapting the skills of a CRO, such as contract negotiation, as leverage in high-level company discussions. After all, money talks, and demonstrating the ability to lead the company to profitability and growth is valuable.
“Nobody should have more market intelligence than you do, so that’s your superpower,” Pickett said. “You can bring anecdotes to the discussion and say, ‘I was just talking to the CEO of this company, and this is how they’re starting to think, I think our product or our strategy should start to point in that direction.”