- The “PayPal Mafia” is one of the most influential clubs in Silicon Valley.
- Historically, mentions of the group never included women who worked at PayPal.
- Here are 20 women who helped build PayPal early on, and the careers they’ve gone on to build.
- See more stories on Insider’s business page.
The PayPal Mafia has long been cited as one of Silicon Valley’s most influential clubs.
Its members — including Peter Thiel, Max Levchin, Reid Hoffman, Luke Nosek, David Sacks, Keith Rabois, and Elon Musk — are a who’s who of powerful players in the tech world who went on to found iconic startups and VC funds.
The group’s moniker was established in a Fortune profile in 2007, which included a photo shoot of the group dressed in leather jackets and tracksuits, playing cards and drinking bourbon — Maker’s Mark, to be precise. The list has since been referenced in network analyses and refreshed lists of the Mafia’s ongoing investments, new ventures, and overall influence on the global tech scene.
The origins of the payments giant started as a race between two of the PayPal Mafia’s most famous members: Elon Musk and Peter Thiel. Musk’s x.com and Thiel’s Confinity were competitors before merging and rebranding as PayPal in 2000.
After a couple scrappy years, PayPal went public in February 2002. But just a few months later, eBay, the venue that PayPal relied on for a significant chunk of its business, announced plans to acquire it in August 2002 in a deal valued at $1.5 billion. In 2015, PayPal would return to the public markets when it was spun out of eBay and relisted as the company it is today.
Most of the members of the PayPal Mafia left the company shortly after the eBay acquisition, but their accomplishments as founders or early employees of PayPal, one of the dot-com bubble’s breakout success stories, can’t be ignored.
But the oft-referenced list of bosses, capos, and consiglieri features mostly members of the executive team, all of whom were men.
Down the chain of command, there were countless others, many of them women, who held critical roles in the company’s early days, from VPs and directors of product to the senior counsel and head of design.
Many have also gone on to be successful in the tech and venture world. But despite their accomplishments, the members of the PayPal Mafia remain the people most often cited with regard to the early days of the payments giant.
“That feeling of watching the stories focused on men, failing to mention women, I think is a very common experience for women in technology and in other fields,” said Rebecca Eisenberg, a former senior counsel at PayPal.
To be clear, the lack of recognition was not a result of PayPal’s internal culture at the time, said those who were there. Insider spoke with eight early, female employees at PayPal, all of whom said they didn’t believe the members of the PayPal Mafia intentionally excluded women.
“As many people have pointed out, the PayPal Mafia doesn’t necessarily highlight women, but that wasn’t my PayPal experience,” said Nellie Levchin, an early PayPal employee and now a venture investor.
Some mentioned unconscious bias as a factor in the tech industry and media’s focus on PayPal’s early male employees versus their female colleagues.
Others pointed to the lack of female founders among the group as a reason for their lack of recognition.
Often, analyses of the legacy of the PayPal Mafia focus on companies members of the group founded and investments they made post-PayPal.
Many members of the PayPal Mafia did go on to found high-profile tech companies and VC firms, including LinkedIn, Palantir, Founders Fund, and Affirm. The group also has ties to countless other funds and companies, such as Facebook, Tesla, Xoom, Yelp, and YouTube.
But for women, starting something from scratch and getting funding was — and still is — an uphill battle.
“A lot of women didn’t go on to found their own companies because it’s really hard to raise money,” said Deborah Liu, an early product manager at PayPal and now the CEO of Ancestry.
Only 14.4% of VC cash invested in the US in 2020 went to female-led or mixed-gender founding teams, down from 16.9% in 2019, All Raise reported. And women represented just 13.3% of check writers at US VC firms.
“I work with many early-stage founders and early-stage companies now. I can see that the bias is real,” said Levchin, who is an investor at SciFi VC.
Still, the women who worked alongside the PayPal Mafia from the company’s founding until eBay’s acquisition held impressive roles post-PayPal. They landed major jobs and board seats at leading tech companies — from Facebook to Google to LinkedIn, to name a few.
“I don’t think starting a company would have been easy for a lot of us,” Liu said, ” but I don’t think any of us have any regrets about the path that we’ve taken.”
Internally, recognition was meritocratic at PayPal
While the external spotlight has historically excluded many of the women who were early employees at PayPal, those whom Insider spoke with said that internally there was consistent recognition for good work.
Receiving praise internally, regardless of gender, was meritocratic. None felt held back within the walls of PayPal.
“It’s really nice to be recognized,” said Huey Lin, an early product manager who’s now working on a climate-change startup and venture investing.
“I was confident that the work would speak for itself, and every time I delivered, people took notice,” Lin said.
The power of the PayPal Mafia is evident in the multiple successful projects members have collaborated on, and the network of former “PayPalians,” a term used to describe former colleagues, has remained strong for more than 20 years since the company was founded.
“We stayed very close because, inevitably, to do such difficult work and make something out of nothing, you need to lean on each other a lot more,” Lin said. “I feel very fortunate to have been a part of that. My time with PayPal has helped shape my entire career and my entire life.”
All these years later, the network has remained tight because of the intensity of the early days at PayPal.
“Anyone that I call ‘medieval PayPalian’ will tell you that we spent most of our life at work. We just didn’t go home,” Lin said. “There was too much to do, and we didn’t want to slow down. We released codes very often. We pushed all the time, which required us to stay at work to ensure everything went smoothly.”
“That type of environment certainly created much deeper and much more trusting relationships,” Lin added.
The bonds built during those early years have proved strong, as many have continued working together in various clusters around the tech industry.
Liu, for one, hired her PayPal colleagues when she moved to Facebook. Lin worked alongside Max Levchin as the COO of Affirm. And Denise Aptekar, another early product manager, said that even today, she frequently works with her fellow PayPalians through her fintech investing.
Insider tracked down nearly two dozen women who played key roles at PayPal in the lead-up to its sale to eBay in 2002 to understand how the experience shaped them, and what they’re up to now.
Meet 20 women who held key roles at PayPal in its early days
Role at PayPal: Vice president, public relations and communications
Years at PayPal: 1999 to 2003
Now: Communications consulting and volunteer work
Anderson joined PayPal as an early employee of Elon Musk’s x.com, where she served as the director of public relations. In March 2000, x.com and Confinity, Peter Thiel’s competing startup, merged and eventually became PayPal.
At PayPal, Anderson continued to lead PR and communications as a VP. As the company grew, operational issues such as frozen accounts and a lack of customer service began causing PR headaches, leading her to temporarily relocate to Omaha, Nebraska. Alongside Sarah Imbach, who led customer-service operations at PayPal, Anderson helped establish a customer-service and fraud-management center.
Anderson left PayPal in 2003 to focus on her family. In the years since, she’s done communications consulting and volunteer work.
Roles at PayPal: Director of product management; director of risk management
Years at PayPal: January 2000 to September 2009
Now: Fintech investor
Aptekar was part of PayPal’s early product-management team, joining in January 2000. She led the development of some of PayPal’s earliest products, including antifraud tools, e-checks, and bank transfers. In 2006, she moved to Tel Aviv, Israel, to oversee PayPal’s acquisition and integration of Fraud Sciences, a fraud-prevention startup.
She left PayPal in 2009, but her experience still informs the career decisions she makes today.
“I learned the fundamentals of how to work in a startup, how to win, and how to create culture in my first few years at PayPal,” Aptekar said.
She was recruited by her former manager at PayPal, Elena Krasnoperova, to join the freelancing platform UpWork in 2013 and held leadership roles in trust and safety, as well as payments.
She left UpWork in August 2019 to organize for Pete Buttigieg’s presidential campaign in Iowa. Now, Aptekar is a fintech investor, backing companies such as Even Financial, TrueAccord, and Wise. She is also a limited partner in 500 Startups, the startup accelerator and investment fund founded by Dave McClure, PayPal’s former director of marketing.
Role at PayPal: Head of data warehousing
Years at PayPal: December 1999 to January 2004
Now: Cofounder of the nonprofit Bharosa Club
Bhargava joined PayPal by way of Elon Musk’s x.com in December 1999. Following its merger with Confinity, she led the creation of PayPal’s data warehouse, reporting to execs such as Max Levchin, one of PayPal’s cofounders.
Since leaving PayPal in 2004, Bhargava relocated to Delhi, India, where she got involved in politics, serving as the chief of staff for a local politician from 2010 to 2015.
In June 2015, Bhargava cofounded an investment platform called Bharosa Club with her husband, Sanjay Bhargava, who is also a former x.com and PayPal employee. The Bharosa Club offers commission-free financial advice at a low annual subscription fee, aiming to simplify finance for consumers in India.
Roles at PayPal: Senior director, global platform; senior director, branded checkout
Years at PayPal: September 2001 to October 2010
Now: Chief experience officer at Bill.com
Chung joined PayPal in 2001 as the director of international and cross-border business. During her nearly 10 years at PayPal, she served as the senior director of its global system, with a focus on PayPal’s international strategy. She led PayPal’s strategy for new markets, adding 17 currencies and enabling money movement in more than 40 countries. Chung then led PayPal’s branded-checkout product, her LinkedIn profile said.
After leaving PayPal in 2010, Chung spent four years at Apple, focusing on payments. She then joined eBay, first as a VP of product management, then as the chief product officer for eBay in South Korea.
Chung joined Bill.com in 2018 and is its chief experience officer, overseeing customer experience for the payments company.
Roles at PayPal: VP of financial services; VP of risk; VP of North America product
Years at PayPal: 2000 to March 2012
Now: VP of global payments and risk at eBay
Cutright spent 12 years at PayPal, serving as the VP of financial services, then as the VP of risk management, and ultimately as the VP of product for North America.
She left PayPal in 2012 to join payments rival Square, where she worked on international strategy. A year later, Cutright joined Plastiq, a payments startup, as its COO. In 2016, she left Plastiq to join eBay, but stayed on as an advisor at Plastiq until 2018.
As the VP of global payments and risk at eBay, Cutright has overseen eBay’s transition to managing payments in-house following the end of its operating agreement with PayPal, which was put in place when PayPal was spun off in 2015.
Roles at PayPal: Senior UI designer; UI design manager
Years at PayPal: May 2000 to April 2004
Now: Senior principal user experience researcher at LinkedIn
Driscoll joined PayPal in May 2000 as a senior UI designer and usability engineer. In 2003, she was promoted to UI design manager, overseeing a team of nine designers.
The following year she joined Adobe as a senior user research specialist. She continued her career in user research at Involution Studios (now known as GoInvo), a design agency focused on the healthcare industry. In 2010, she joined LinkedIn, the professional and social network cofounded by Reid Hoffman, PayPal’s former COO.
Driscoll has been at LinkedIn for more than 10 years. She is now a senior principal user experience researcher.
Role at PayPal: Senior counsel
Years at PayPal: July 2001 to March 2007
Now: Founder and principal at Private Client Legal Services
Eisenberg joined PayPal in July 2001. As the senior counsel, she oversaw major transactions during the early days at PayPal, including its IPO in February 2002 and its merger with eBay, which closed in October 2002.
Since leaving PayPal in 2007, Eisenberg has served as the general counsel at Pure Digital Technologies, where she oversaw its $600 million merger with Cisco. She then joined Trulia as its first general counsel, preparing the company for its 2012 IPO. In 2011, she joined Yishan Wong, a former PayPal engineering manager, at Reddit as the general counsel, overseeing its spinoff from Condé Nast.
Wong was the CEO of Reddit at the time. Now, he’s the CEO of Terraformation, the environmental startup where Huey Lin also works.
In 2020, Eisenberg ran for Palo Alto City Council, but did not win a seat.
Since 2009, she has also owned and operated a boutique law firm, Private Client Legal Services, where she assists executives, entrepreneurs, and engineers with large personal transactions and employment agreements, with a focus on private company stock.
Roles at PayPal: Senior manager of global content; director of product development
Years at PayPal: January 2001 to October 2012; July 2015 to present
Now: Senior director of IT services and employee technologies at PayPal
Grasham has had a long run at PayPal: She joined in January 2001 and stayed with the company through the eBay acquisition and subsequent spinoff.
She started as a senior manager of global content, but held roles in operations and strategy, and was a director of product development, implementing new customer-service software from 2009 to 2012, her LinkedIn profile said.
As a senior director of strategy and business operations at eBay from 2012 to 2015, Grasham oversaw its IT strategy and managed employee engagement and communications. She was then the program lead for PayPal’s spinoff from eBay in 2015, staying with the payments giant.
Grasham is now the senior director of IT services and employee technologies at PayPal, overseeing internal tech transitions globally.
Role at PayPal: SVP of customer-service operations and fraud
Years at PayPal: February 2000 to May 2002
Imbach led the creation of PayPal’s customer-service organization from February 2000 to May 2002, establishing its customer-service center in Omaha, Nebraska, which remains a key office for PayPal.
After leaving PayPal in 2002, Imbach was an operations consultant for two years before joining LinkedIn as its COO from 2004 to 2007. She then spent a little more than a year as LinkedIn’s VP of revenue and customer operations before leaving in 2009 to join 23andMe as the COO.
Imbach left 23andMe in July 2010. She has since been an angel investor and advisor, backing companies focused on operations, such as Docugami, Twine, and Undock, Crunchbase showed.
Roles at PayPal: Director of user interface; VP of product design
Years at PayPal: March 2000 to July 2003
Now: Director of UX at Google
Lee joined PayPal in March 2000. She managed user-experience teams and spent a six-month stint as the director of product marketing during an early reorganization.
She oversaw the redesign from PayPal’s original PalmPilot-focused offering to its broader, online payments product.
Since leaving PayPal in July 2003, Lee has served as a UX lead at companies such as
and Oculus VR. Today, Lee is Google’s director of UX, overseeing the search app and news.
Roles at PayPal: Financial-system product management; FP&A
Years at PayPal: September 2000 to September 2003
Now: Investor at SciFi VC
Levchin joined PayPal as an intern after graduating from California State University, East Bay, first working with cofounder Luke Nosek on competitive market research. She then moved into financial-system product management, working with people such as Huey Lin and Denise Aptekar. Ahead of PayPal’s IPO, Levchin transitioned to financial planning and analysis.
Levchin left PayPal in September 2003, following the eBay acquisition. She joined Peter Thiel’s hedge fund, Clarium Capital Management, as the director of operations before becoming the chief risk officer in 2008. There, she worked with her former boss Jason Portnoy, who was previously the VP of FP&A at PayPal.
Levchin left Clarium in 2010, working as an advisor for early-stage companies, and joining the boards of nonprofits. She established an incubator, HVF Labs, with her husband, Max Levchin, a PayPal cofounder and now the CEO of Affirm.
In 2017, the couple formalized their investing, cofounding SciFi VC, an early-stage fund that backed startups such as Brex, Coinbase, Gusto, and Stripe.
In some ways, her experience at PayPal informs her investment decisions today, with a particular focus on the founding team, Levchin said.
“I do look for a PayPal-like pattern. Is the team cohesive? Is there a lot of trust? Is there a lot of openness among the team? Is it driven, without being aggressive? These are traits that any company needs. We had those at PayPal, so it’s easy to scan for them,” she said.
Roles at PayPal: Product management; operations leadership
Years at PayPal: March 2001 to October 2012
Now: VC at GGV Capital; special projects at Terraformation
Lin joined PayPal in March 2001 and spent over a decade in key leadership roles. She was one of PayPal’s first product managers, responsible for customer experience and marketing, as well as expanding PayPal’s risk-management framework in Europe. In her last role, she ran Asia-Pacific operations and was the general manager of Shanghai operations, which at the time included oversight of more than 800 people.
In 2012, she was recruited by Max Levchin and moved back to the Bay Area to join Affirm as its founding COO, where she built the company’s customer and business operations. Lin moved back to Asia with her family in 2018. She worked as the president of Asia for Flexport, a freight-tech company. It was fellow PayPalian Chris Ferro, the chief legal officer at Flexport, who introduced her to the company.
Lin, who lives in Hong Kong, is now a venture partner at GGV Capital. She’s also working with former PayPalians, including Yishan Wong and Yee Lee, on a new company called Terraformation, an environmental startup focused on global forest restoration to help solve the climate crisis.
She said the big wins at PayPal early in her career fostered a unique level of confidence as she moved on: “That success gave me that first piece of confidence I needed to take additional risks. That, along with the incredible network we all developed, is priceless.”
Roles at PayPal: Director of product; director of corporate strategy,
, and charity
Years at PayPal: June 2002 to March 2008
Now: CEO of Ancestry
Liu was studying at the Stanford Graduate School of Business and interning at eBay when she stumbled upon PayPal at a career fair. After meeting with Tim Wenzel, PayPal’s first recruiter, and Katherine Woo, a director in the product organization, Liu was invited to visit the PayPal offices. She ended up having dinner with Peter Thiel and David Sacks, PayPal’s COO, who convinced her to join.
In June 2002, a few weeks before the eBay acquisition was announced, Liu started as PayPal’s senior product manager.
Liu was ultimately promoted to director in product management, overseeing PayPal’s marketplace strategies. She then led development in PayPal’s social-network and charity-payments strategies.
The legacy of those products still exists, with PayPal processing record-breaking donations though its charity system on Giving Tuesday in 2020.
“To think that we have a small fingerprint in what the company has become is incredible,” Liu said.
In 2008, Liu moved to the eBay side as a product manager focused on the buyer experience. She left in 2009 to join Facebook, where she started as the product-marketing manager for consumer monetization. She then managed its payments and commerce strategy, developing Facebook Marketplace and Facebook Pay.
Liu left Facebook to join Ancestry as CEO in March 2021.
Liu is also the founder and chairman of Women in Product, a network of 17,000 women in tech that hosts annual conferences and events around the country.
Role at PayPal: QA engineer
Years at PayPal: January 2000 to November 2006
Now: Manager of QA at Ironclad
Pok was an early engineer at PayPal, joining in January 2000. She spent almost seven years as a quality-assurance engineer before leaving in November 2006 to join Palantir, her LinkedIn profile said.
Palantir was cofounded by Peter Thiel along with Nathan Gettings, a former PayPal engineer. Gettings would go on to cofound Affirm with Max Levchin in 2012.
Pok was a senior software quality engineer at Palantir until July 2015, when she joined Ironclad, a legal-tech company founded by Jason Boehmig and Cai GoGwilt, who was also an engineer at Palantir from 2011 to 2014.
Roles at PayPal: Manager of product resource planning; senior organizational development business partner for PayPal and eBay
Years at PayPal: October 2001 to October 2005; April 2010 to May 2015
Now: People business partner and director at Glassdoor
Proctor started at PayPal in 2001 as a product manager, leading the development of PayPal’s credit-card-processing capabilities. She then led the team that oversaw credit, debit, and automated clearing house processing. In 2004, she transitioned to lead resourcing and planning for PayPal’s 500-person product-development organization, her LinkedIn profile said.
After leaving PayPal in October 2005, she worked for years as a consultant before rejoining in 2010. Proctor eventually became the senior organization development business partner, overseeing all things human resources for 4,000 PayPal employees, her LinkedIn said, before shifting focus to 3,500 eBay employees. She developed the annual review process and oversaw the onboarding for new VPs, among other employee-development initiatives.
In addition to being an executive coach and leadership consultant, Proctor now serves as a people business partner at Glassdoor, working with engineering, product, and IT leaders on hiring and retaining talent.
Amy Rowe Klement
Role at PayPal: VP of product
Years at PayPal: September 1999 to 2006
Now: Managing partner at Imaginable Futures
Klement joined PayPal as one of its earliest employees in September 1999. As the VP of product, she was involved from the start in developing PayPal’s payments systems. She also facilitated the company’s expansion into Europe and Asia, and worked on the launch of PayPal Mobile.
In 2007, Klement transitioned to the eBay side of the business. She led relationship marketing, then product strategy and operations.
She left eBay in October 2009 and spent years serving on the boards of multiple companies and nonprofit organizations. She maintains seats on the boards of Bridge International Academies, Andela, Imagine Worldwide, and Teach for All, her LinkedIn profile said.
In January 2020, Klement became the managing partner of Imaginable Futures, a philanthropic investment firm spun out of Omidyar Network, an impact-investing firm.
Role at PayPal: VP of fraud
Years at PayPal: 1999 to 2002
Schultheis was PayPal’s first female employee. She originally interviewed for an office-manager position, but ultimately served as PayPal’s VP of fraud from 1999 to 2002.
Now, Schultheis is a consultant with expertise in organization restructures, team management, and infrastructure and strategy development, her LinkedIn profile said.
Role at PayPal: VP of finance
Years at PayPal: January 2000 to April 2003
Now: Head of finance at Autonomic
Teng joined PayPal in January 2000 as the VP of finance.
Since leaving PayPal in April 2003, she has held leadership roles in finance at Palantir, the note-taking app Evernote, and All Turtles, an AI startup.
Teng is now the head of finance at Autonomic, a cloud system for connected cars and apps.
Roles at PayPal: Operations; customer support; accounting
Years at PayPal: February 2000 to May 2004
Wong joined PayPal in February 2000 to work in operations and customer support. She then moved into accounting roles before becoming a senior accountant from 2001 to 2004, her LinkedIn profile said.
She left PayPal in 2004 to join Xoom, a competitor, as an accounting manager. Xoom was backed by Peter Thiel and Sequoia’s Roelof Botha, a former CFO of PayPal, and went public in 2013. It was acquired by PayPal in 2015.
Wong left Xoom in 2015. She went on to serve as a controller at Prosper, Tophatter, and Cred. She left Cred in October 2019. She’s now a finance consultant for startups.
Roles at PayPal: Director of merchant services product; director of product strategy and experience; senior director of core consumer strategy
Years at PayPal: February 2002 to November 2006
Now: Head of Airbnb.org
Woo joined PayPal in February 2002, right around the time of its IPO and months before the eBay acquisition was announced.
She served as the director of merchant services before moving on to product strategy and experience. In May 2006, she became the senior director of core consumer strategy. Woo then transitioned to the eBay side of the business. She was the chief of staff to Meg Whitman, who was the CEO at the time. Then she became the senior director of product strategy and operations for eBay North America, her LinkedIn profile said.
Woo cofounded Sofa Labs, a social-app developer, and CoupRecoup.com, a coupon marketplace. In 2011, she joined Kiva, a microfinance nonprofit, as the head of product.
In 2015, Woo joined Facebook, first as a product lead for social good, then as the director of product management for Facebook Groups. In August 2019, she joined Airbnb, where she’s the head of Airbnb.org, the company’s nonprofit arm.