Pinterest Chief Executive Bill Ready is a Silicon Valley veteran who traces his business roots to his childhood in Elizabethtown, Ky., where as a teenager he got a job sorting mail for a local telephone-payment firm named Call Me Bill.
While many of his peers didn’t go to college after high school, Ready credits that early work experience in a corporate setting with driving him to pursue a different path. Still, he never imagined that he’d one day be running a publicly traded company with thousands of employees.
The first in his family to graduate from a university, and later business school, Ready merely hoped that he could find a way to afford health insurance and a pair of Air Jordan sneakers. Now, when he wears one of the many sets of Jordans he owns, they serve as a reminder of his humble beginnings.
Ready, now 44, joined Pinterest in 2022 from Alphabet’s Google, where he led commerce and payments for about two years. Before that he served as operating chief of PayPal, after it acquired two other payment companies he ran, Venmo and Braintree. Earlier in his career, he was executive in residence at venture-capital firm Accel Partners and president of another payment business called iPay Technologies.
Pinterest was in a state of turmoil when Ready was named CEO. He replaced a founder who was stepping down after more than a decade and activist investor Elliott Investment Management had just taken a large stake in the social-media company. It was shedding users following a pandemic growth spurt and ad spending across digital media had been slowing down due to changes to Apple’s App Store privacy rules.
Ready has since worked to build a relationship with Elliott, replenish the company’s C-suite and improve its finances. He mainly posts photos of his sneaker collection and basketball content to Pinterest. The company’s valuation has more than doubled during his tenure to around $28 billion. Its revenue was $3.1 billion last year, up about 9% from 2022. The company also reported a net loss of $36 million last year, compared with a loss of $96 million in 2022. Ready lives near the company’s San Francisco headquarters with his wife, their 10-year-old daughter and a dog.
Here are four of Ready’s most trusted advisers:
Ready was PayPal’s operating chief when he met Alber at a dinner for executives in the Bay Area. Alber started up a conversation with Ready about how she preferred doing business with Venmo over PayPal, not knowing PayPal owned Venmo or that Ready had been CEO of Venmo before PayPal bought it in 2013.
After the dinner, Ready said he shared Alber’s insights with his team at PayPal and they ended up incorporating some of her ideas in the company’s products. “He’s a very good listener,” said Alber. “Some people are so set on their vision, they don’t take into account other people’s ideas and see it just as criticism. Bill sees constructive feedback.”
The executives stayed in touch from then on, and in 2020, while Ready was at Google, he accepted a seat on Williams-Sonoma’s board. After board meetings conclude, he sometimes asks Alber to grab coffee so he can pick her brain on business matters.
When he joined Pinterest, Ready asked for her take on his intent to abandon his predecessor’s plans to move into e-commerce transactions.
“That pivot in our strategy is something I discussed a lot with Laura,” said Ready, adding that he also turns to Alber for advice on which new shopping trends Pinterest should pursue. “She has a fantastic feel for consumers,” he said.
Alber recalled giving Ready similar feedback during his time at Google. “He has great instincts,” she said. “I’ve tried to recommend he stay focused on those instincts.”
Nearly a decade ago, while still leading ADP, Rodriguez set out to modernize the payroll giant’s technology infrastructure in part by adding tech-industry gurus to its board. Ready was among a handful of such recruits and by far the youngest, then in his mid-30s and leading product and engineering at PayPal. “For us, it was a coup to be able to get him,” said Rodriguez.
Today, Ready considers himself just as fortunate for getting to know Rodriguez, who’s now retired and lives in New Jersey. From their opposite sides of the country, they talk by phone a few times a year about leadership issues, such as how Ready can drive growth at Pinterest while staying true to its culture and mission.
Established in 1949, payroll-processing giant ADP is “the kind of business that still embodies the values of the founder but also has been really successful over the long term,” said Ready. “Those are things that I’m looking to learn from Carlos.”
More recently, Ready has sought Rodriguez’s wisdom on how to get along with board directors now that he’s the one in the CEO seat.
“My advice to him is cliché: The buck stops with him,” said Rodriguez. “As CEO, you have to be decisive.”
In the late 1990s, Bowers was building the bill-payment company iPay Technologies and in need of a software engineer. Ready was pursuing his bachelor’s degree in information systems and gladly stepped up to the plate. “She gave me my first chance,” Ready said.
A friend who was related to Bowers had made the introduction, though Ready already knew her—she had also founded Call Me Bill, the telephone-payment firm where he worked as a teenager. They just didn’t interact back then.
Years later, after working at other companies such as insurance giant Humana and consulting firm McKinsey, Ready returned to iPay, this time as its finance chief before becoming president, as Bowers made the transition to a less active role. “Even though he was young, he quickly demonstrated he was more than capable of taking the company to the next level,” said Bowers, who now runs Venminder, a third-party risk-management platform.
Ready said he learned a lot about entrepreneurship from both stints at Bowers’s companies. Now he dials her number whenever “there’s no textbook answer” to a challenge he’s trying to solve, he said.
One such instance occurred when he was CEO of Braintree and was struggling to decide whether he should accept an acquisition offer from PayPal or stay independent. “Her advice was: Do what you think is going to help you build what you told your customers you are going to build,” he said. “She’s been an amazing mentor.” He ended up accepting the takeover bid.
Since social media in general has been widely criticized as harmful to people’s mental health, Ready wants Pinterest to have a positive impact on its users’ lives. Soon after he signed on as CEO, he sought help in this area from Rich, a digital-wellness expert who thinks social media can be beneficial or harmful. Together they came up last year with the Inspired Internet Pledge, an industrywide initiative to create a safer and healthier internet.
“I wanted to spark a movement around this,” said Ready. “I’d love for us to wake up in a world where social-media companies are competing on their safety standards,” as opposed to the amount of time people spend on their platforms.
Nowadays, Ready occasionally calls Rich to get a report card on how Pinterest is doing in its efforts to support the mental health of its users. Rich said it’s clear that Ready is eager to please more than just shareholders, advertisers and users. Ready also wants to make Pinterest safe for his own daughter.
“He’s coming to this with skin in the game,” said Rich.
Write to Sarah E. Needleman at Sarah.Needleman@wsj.com
