The Information’s Latest Free Agents

In this round, we profile seven people, from 30-somethings fresh out of the whirlwind of the startup world to 50-somethings mapping out their next moves amid fruitful careers at blue chip firms like Hewlett Packard Enterprise.

To read previous installments of Free Agents, with profiles of execs from Twitter, Intel, HBO, Snapchat and others, click here. 

Nikesh Arora

Last full-time job: President and COO, SoftBank, mid-2014 to mid-2016

Self-description: “Operator at scale”

Age: 48

Born: Ghaziabad, India

Current residence: Atherton, California

Career highlights: After graduating from the Indian Institute of Technology in Varanasi with an electrical engineering degree, Mr. Arora moved to the U.S. to get a master’s in business from Northeastern University, then a finance degree from Boston College. He stayed in the Boston area to become a financial analyst in the IT department at mutual fund giant Fidelity Investments before becoming a buy-side analyst at Putnam Investments nearby. He took off for Germany to work on mobile data services for wireless carrier T-Mobile, eventually taking the role of chief marketing officer for Europe. Two months after he left that job, Google, fresh from its 2004 IPO, came calling for a president of its Europe business operations. After his peers Tim Armstrong left to lead AOL and Sheryl Sandberg left to be No. 2 at Facebook, Mr. Arora ascended to chief business officer in 2009. He left in 2014 for a big role at SoftBank, the Japanese conglomerate.

Biggest accomplishment: Scaling Google’s ad business, “hiring the best people and creating a culture of excellence,” he says. He helped build up a display-advertising business “from scratch,” he says, following Google’s then-monster acquisition of DoubleClick. He says he also played a key role in buying and later selling Motorola Mobility, the phone maker, on Google’s behalf. While he was willing to be confrontational with Google’s product leaders at times, he was credited with consistently hitting goals and commanded respect throughout the 15,000-plus sales organization. Annual revenue more than doubled during his five-year reign, to $50 billion.

Biggest disappointment: Not getting the top job at SoftBank after CEO Masayoshi Son earlier said Mr. Arora would inherit the role. On the plus side, he invested more than $4 billion in two years, including in Didi Dache (now called Didi Chuxing) and lending firm SoFi, and helped sell more than $20 billion in assets, including game maker Supercell, earlier this year. But the sums he spent on some India startups, including Snapdeal and Housing.com, and the valuation he accepted as part of those deals, have been widely questioned. “It’s too early to judge,” he says. He says Mr. Son changed his mind about relinquishing the CEO role, precipitating his departure.

What he’s doing now: Spending time with his three children, including a newborn; getting “a little healthier” and traveling.

What’s next: He prefers to be CEO of a growing company. “I'll go anywhere as long as it’s something I'll have fun doing.” He’s open to joining an older industry too. “Every business has a strong technological component now,” he says.—Amir Efrati

Molly Turner

Last full-time job: Global head of civic partnerships at Airbnb

Self-description: “I first and foremost consider myself to be an urban planner. I’m just moonlighting in the tech world.”

Age: 33

Born: Berkeley, California

Current residence: San Francisco

Career highlights: After earning degrees from Dartmouth and Harvard, the Bay Area native briefly worked as a consultant for cities trying to manage tourism development. She also worked in San Francisco’s economic development office. Ms. Turner joined Airbnb in 2011 as the first employee in its public policy division. A few months after she joined, the company launched across Europe, now its biggest market. In 2014, she worked with Amsterdam officials to pass the first major law to allow home sharing. “I flew back and forth monthly to sit down face to face to walk through the data and all the iterations of what we should do,” she says. “It entailed approaching cities with empathy.”

Biggest accomplishment: Last year, Ms. Turner helped spearhead the company’s entrance into Cuba, beating big hotel chains to a country that’s now popular with American tourists and one of Airbnb’s fastest-growing markets. “So many U.S. businesses take an imperialistic approach to Cuba, making sure they need to take an American way of doing things there. We took an opposite approach, adapting our business to Cuban people.”

Biggest disappointment: She regrets that the relationships she built with cities have grown more contentious lately “because of a lot of strong external political forces,” she said. “We’ve gotten caught up in some political battles much bigger than us.” The company has legal battles brewing with San Francisco and New York over the cities’ moves to impose fines on hosts.

What she’s doing now: Ms. Turner will teach a course in urban innovation and entrepreneurship at University of California at Berkeley’s Haas School of Business. She is also consulting for startups focused on relationships with cities. She still sits on the boards of Tumml, an accelerator for urban-focused startups, and SPUR, a Bay Area urban-planning think tank.

What’s next: “I’d like to continue helping entrepreneurs figure out how to wield technologies to make cities better, but make sure they do it to thoughtfully impact cities and not just help their own users.—Cory Weinberg

Tom Staggs

Last full-time job: COO of The Walt Disney Co. from 2010 to April 2016

Self-description: “If you’re feeling really comfortable doing your job, then you’re not pushing yourself enough.” 

Age: 55

Born: Excelsior, Minnesota

Current residence: Los Angeles area

Career highlights: After beginning his career as an investment banker at Morgan Stanley, he joined Disney in 1990, hired by then-CEO Michael Eisner and COO Frank Wells to help lead the company’s mergers and acquisitions team. He played a key role in a number of Disney acquisitions, including the purchase of Capital Cities/ABC in 1995. He went on to become Disney’s CFO, overseeing other acquisitions like Pixar. He later managed the theme parks division during a period of major expansion, including the opening of Shanghai Disneyland. He was named COO in 2015, making him the heir apparent to CEO Bob Iger. But earlier this year he stepped down from the role once it was officially decided he wasn’t going to be given the CEO job. He’s been in an advisory role at Disney since and will leave the company at the end of the month.

Biggest accomplishment: As an M&A lead, he helped put together multiple transformative deals for Disney in the last 25 years. The top of that list was the Capital Cities/ABC deal, which gave the media firm both network and cable outlets (like ESPN) that today comprise much of the company’s profits. Other acquisitions that he played a hand in—like Marvel, LucasFilm and Pixar—have proved vital to Disney’s ability to churn out a steady stream of franchises.

Biggest disappointment: Despite being named to the successor position of COO, Mr. Staggs seemed to suffer the fate of many other Disney heirs apparent. Though largely well-liked and respected at Disney, it appears Mr. Iger wasn’t yet willing to pass off his CEO duties to another person. Though the two stated they’re parting on good terms, Mr. Stagg’s resignation was a disappointing end to a 25-year career at the company.

What he’s working on now: Still a Disney employee until the end of the month, he’s been in advisory role at the company and hasn’t taken on any outside roles or duties during the period.

What’s next: There don’t appear to be any immediate plans other than spending time with his family. He’s still interested in the next wave of technology as it affects content and distribution.—Tom Dotan

Manish Goel

Last full-time job: Hewlett Packard Enterprise’s senior vice president and general manager of storage from March 2015 to August 2016

Self-description: “I’ve got a very strong combination of strategic thinking, operational expertise and an ability to get things done.”

Age: 52

Born: Dehradun, India

Current residence: Los Gatos, California

Career highlights: Mr. Goel has had a varied career which encompasses seven different industries and multiple different functional roles. He’s been an electrical engineer, a software engineer, a strategic consultant, a business development executive, a startup CEO and, for the past 13 years, a high-ranking storage executive at two Fortune 500 companies. As executive vice president of product operations at NetApp, Mr. Goel led product and technology strategy for an organization with more than 5,000 people. And HPE’s storage sales grew during all six quarters he spent at the company.

Biggest accomplishments: Mr. Goel says he’s proud of helping NetApp diversify its storage line to include multiple different products. This was a significant strategy shift for NetApp that required changes across the entire company, he says. More broadly, Mr. Goel says he has learned much about the skills required to be a good manager from NetApp Vice Chairman Tom Mendoza, one of his mentors. “Tom once told me, ‘People don’t care what you know unless they know you care.’ That really became a guiding light for me,” said Mr. Goel.

Biggest disappointment: In 2001, when he was vice president of business development at Copper Mountain Networks, Mr. Goel says he had to lay off “a very good personal friend” due to the economic downturn at the time.

What he’s doing now: Mr. Goel says he’s having conversations with multiple different parties, which he wouldn’t name, about potential employment opportunities.

According to Mr. Goel’s LinkedIn profile, his current company is “Hammock,” and his job description is “Working on the handicap. Navel gazing. Debating whether to join the Facebook revolution or stay safely ensconced in the dark ages.”

What’s next: Mr. Goel says his next job will be “something that is intellectually challenging and interesting,” and probably won’t be in the enterprise technology market. He’s particularly interested in self-driving cars and the Internet of Things. “Ideally, I’d love to find myself in conversations that are going to be relevant over the next couple of decades,” says Mr. Goel.—Kevin McLaughlin

Betsy Morgan

Last full-time job: CEO of The Blaze from 2011 to 2015

Self-description: “I've had the very good fortune to lead two transformative digital-native publishers, and here is what I know: There is great value in the power of The Tribe.”

Age: 48

Born: Suffield, Connecticut

Current residence: New York

Career highlights: She began as a media and entertainment banker, and later moved to CBS News on the business side. She was part of a group making investments in web ventures like SportsLine and MarketWatch. In 2007, she was hired by The Huffington Post as its first CEO. While there, she expanded the site into other verticals beyond politics. She left in 2009 after a dispute with other top management and soon joined The Blaze, the media company founded by conservative pundit Glenn Beck. She led The Blaze’s expansion on the web, branching off into lifestyle categories, and also grew it into a video streaming service that was picked up by some cable providers. She left in 2015 and has recently been working as an entrepreneur-in-residence at Aryeh Bourkoff’s boutique banking firm LionTree.

Biggest accomplishment: As The Huffington Post’s first CEO, she took the company from a fledgling website to one with significant revenue and legitimacy as a news outlet. In the 2008 election, The Huffington Post was given credentials to join the presidential press corps—the first digitally native journalist allowed into the group. In her time as CEO she also helped grow the company’s traffic and revenue; The Huffington Post made $30 million in 2010, the year before it was acquired by AOL.

Biggest disappointment: Her tenure as the CEO was cut short after a disagreement with the site’s co-founders Ken Lerer and Arianna Huffington. She describes the split as arising from a “difference of opinion,” as to the direction of the company after it had raised a funding round from Oak Investment Partners. Ms. Morgan was ultimately replaced by board member Eric Hippeau. She says she’s on good terms with both Mr. Lerer and Ms. Huffington. She also regrets turning down an opportunity to work for Apple in a position under Eddie Cue.

What she’s working on now: In her current position at LionTree she advises the firm’s digital media clients on M&A strategies. She’s also serving on the board of several companies including analytics firm ChartBeat and e-commerce infrastructure startup CommerceHub.

What’s next: She’s been advising a number of digital publishers like the Player’s Tribune, Barstool Sports and theSkimm. She isn’t planning on starting a company on her own but would be happy to keep advising. “I'm more valuable helping companies that exist today get to the next level and thrive.—Tom Dotan

Dana Wagner

Last full-time job: General counsel at Square since 2011

Self-description: “I’m a mission-driven person who enjoys solving complicated problems. I love building and managing great teams.”

Age: 41

Born: East Coast, but considers home Champaign–Urbana, Illinois

Current residence: San Francisco

Career highlights: After completing law school at Yale University, Mr. Wagner clerked for Judge Merrick Garland, nominated by President Obama for the Supreme Court earlier this year. Mr. Wagner then spent eight years working for the U.S. Justice Department, first as a trial attorney in its antitrust division and later as a criminal prosecutor going after organized criminal groups and high-volume drug dealers. He moved to Google in 2007, working on competition and antitrust issues for the company. “When I interviewed for my first private-sector job at Google and they asked me what skills from my current job would be applicable to this job, I said, ‘Well, I hope none of them,’” Mr. Wagner says.

Biggest accomplishment: Mr. Wagner joined Square early on and was responsible for building out all of the company’s legal and policy operations. He established teams for lawsuits, government relations, trust and safety and regulatory compliance, about 100 people in total. “I couldn’t be prouder” of those teams, he says. “They’re full of wonderful, talented people who take their work very seriously but don’t take themselves too seriously.”

Biggest disappointment: As Mr. Wagner has moved into a management role and away from specialties like antitrust, he doesn’t get to roll up his sleeves and dig into the details of legal issues as much as he used to. “I like to read and edit a brief, or review a contract thoroughly, or be the one to run points on a government meeting from time to time to make sure I still have those skills and make sure I’m still adding value in that way,” he says.

What he’s doing now: Mr. Wagner is still technically at Square for several more weeks, so he’s working to ensure that the transition is as smooth as possible. (The company has yet to announce his successor.)

What’s next: “I’m kind of excited not to know what’s next. In the short term, it’s unwinding a bit, reconnecting with people and interests and things outside of work I’ve probably neglected a bit over the last few years.” Mr. Wagner aims to get back into work eventually but he’ll “take his time and be thoughtful” about his next move.—Steve Nellis

Tawny Holguin

Last full-time job: Partner, Andreessen Horowitz, 2014 to March 2016

Self-description: “I value relationships above all and have found my career passion in supporting entrepreneurs tackle big problems and build their dream businesses.”

Age: 31

Born: Napa Valley, California

Current residence: San Francisco

Career highlights: Fresh out of Harvard, Ms. Holguin joined an e-commerce startup called Mercantila in 2007. After that she had a stint working in digital media for Boston-based ad agency Mullen. She returned to tech in 2010 and became an early employee at AngelList. From there, she met John Poisson and became the first employee of his gift-giving business, Wantful. She helped build the company to 30 people before it shut down. She then joined Andreessen Horowitz as a business operations partner, focused on their early stage investments.

Biggest accomplishment: Building a new function within Andreessen Horowitz’s business operations team that gave assistance to the early and seed-stage companies that received investments from the firm.

Biggest disappointment: While Ms. Holguin was running operations and product management at Wantful, the company’s consumer and corporate businesses began to take off. But the company was stretched too thin when it began focusing on strategic partnerships with companies like Nordstrom. Wantful shut down in 2013. She believes it should have had a more successful outcome.

What she’s doing now: Currently a strategic adviser to FounderMade, a New York-based company aimed at helping startup founders grow their businesses.

What’s next: Aside from consulting, Ms. Holguin would like to join a company full-time in the right role.—Reed Albergotti