Junko Swain Empowers Freelancers Across the Globe

Junko Swain has taken two companies public and now as Upwork’s chief accounting officer, she wants to help develop the next generation of talent

Photo by Michael Scorsur Photography

Junko Swain made the decision to emigrate to the United States on her own. The first-generation American left Japan because of what she saw as a limitation on her career ambitions after working in the fashion industry there. “I think most women were expected to serve tea, get married, and quit,” Swain explains. “I really wanted to see what I could and what I was capable of.” Swain would cross the Pacific, study accounting, earn her CPA, and see if she were up to the task.

Thus far, Swain’s accomplishments include helping two companies go public, the top of the mountain for any chief accounting officer—and she’s done it twice. Swain spent five years at eBay in the early 2000s, whose valuation is most easily characterized by a hockey-stick graph. In those five years, the company jumped from $1.2 billion to $8 billion in net revenues, requiring exponential internal growth and stretching by the company’s finance team. It was Swain’s most valuable proving ground and provided the foundation for the rest of her career.

After her second successful IPO, Swain says it might seem odd that she remains at Upwork, where she has spent the past five years leading its accounting function, initially as its corporate controller and now as its chief accounting officer (CAO). “If I wanted to just take another company public, I have plenty of other opportunities, but I just love the mission of this company,” she says. “Upwork aims to create economic opportunities so people have better lives, and that’s why I’m still here.”

Walking the Walk

Upwork’s work marketplace helps connect freelance talent with businesses. That includes business functions at Upwork. When Swain joined, she had only full-time employees. Even through the company’s IPO process, she extended her team by utilizing Upwork’s network of independent talent and continued to grow her team with freelance talent even for critical functions like payroll and Security and Exchange Commission reporting. Upwork supports engaging independent talent in a variety of ways to fit every need it has, from short-term consulting projects to ongoing employment relationships through a staffing provider.

Junko Swain
Junko Swain, UpworkPhoto by Michael Scorsur Photography

“I think one of my biggest accomplishments at Upwork has been helping to achieve the mission our company was founded on,” Swain says. “You can utilize a hybrid workforce and get everything done that you need to get done and done well.”

Finding ideal independent talent is made easier, not harder, by the fact that geographic lines no longer matter. “When you used to go looking for people, those people had to be in proximity of your offices,” the CAO says. “Independent talent on Upwork thrive on the fact that they can be anywhere to do their work. My team is global.”

The value that Upwork has added to freelancers globally can be hard to quantify, but Swain remembers the exact moment when she understood the lives her company is able to improve.

The CAO says an email from a freelancer working for her team one Christmas left an indelible mark on her own mission. “This person told me that before Upwork, they were in danger of losing their home,” Swain says. “Now they’ve been able to put their child through school and have found some security. It was a beautiful moment I’ll never forget.”

The Upwork platform also means engaging and hiring independent talent incredibly quickly, so the average time an independent talent onboards is about a week. Given the company’s massive growth, Swain’s team is now evenly split between full-time employees and freelancers. Swain says that Upwork has helped create a truly equal playing field for talent who can opt for rewarding work with top companies regardless of their location, their ethnicity, or their gender.

True Equality

Diversity is important to Swain for many reasons that can be understood by her decision to emigrate to the United States. “When you think about minorities, I’m a first-generation minority who speaks English as a second language; I’m a wife and mother and working professional. If there is a list, I think I probably mark off most of the boxes,” Swain says, laughing. “I feel privileged to be able to talk about these issues that are important to me.”

 “One of my biggest accomplishments at Upwork has been helping achieve the mission our company was founded on.”

The CAO says she is passionate about helping develop talent because of the opportunities she was presented early in her career at her former employer. “At the time, eBay was really focused on developing its next generation of leaders,” Swain says. The CAO is the very product of that focus, and her acknowledgement of those who have helped her along the way has made gratitude a daily exercise.

She says that if she sees motivated talent, she’s going to get involved. “This doesn’t come down to race or background or orientation,” Swain says. “I want to provide an equal opportunity to help lift up whoever wants to get to the next level. There were people early in my career who did that for me, and I’m now at the point in my career where I can do that for someone else.”

Swain crossed an ocean, learned a new language, and took on the world. She wanted a better life, and now at Upwork, she’s making the same happen for millions of the work marketplace’s users.