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Voices Amplified: Upwork’s CAO Junko Swain on Platforms, Data, and Machines

SEC Reporting
Q&A with Junko Swain, CAO of Upwork
5 min read
Published: October 12, 2021
Last Updated: April 25, 2023

As Chief Accounting Officer at Upwork, Junko Swain knows all about making connections. Upwork helps enterprises simplify their business operations by connecting them with top freelancers from all over the world for anything from short-term projects to long-term work. At the end of the day, it’s about community building, efficiency, and problem-solving. Junko has startup and multi-billion dollar corporation experience with two IPOs under her belt, and is adept at sharing her perspectives to help others see possibilities in growth, big-picture thinking, and best practices in accounting and compliance.

Junko's wealth of experience made her a terrific fit for the 2021 Workiva Amplify conference, which attracted more than 8,000 participants from around the globe who wanted to explore the theme: Dare to simplify. Here are some highlights of our sit-down with Junko. 

Key Takeaways: 

  • Real-time data is critical for decision-making, with accuracy being the most important driver of business direction
  • Choosing the right platform and technology can drastically reduce the time in closing the books
  • A prediction for the future: Machines and bots to help enterprises simplify complex systems, along with keeping an open mind 

Q: The pace of business is increasing. Can you tell us what operating complexities are top of mind for you in responding to the greater demands for transparency?

A: Speed scares me, right? Because when I look back at the last 25 years, the pace that technology is changing and how quickly we need to transform the organization, it's enormous. It's no comparison. And when I think of the next five, 10 years, it's going to be much faster. So my focus is how we can give real-time data, not only real-time but accurate data, so the executive team can pivot the business direction. Easy to say, but with so many systems that feed the data, it has been really, really complex.

Q: Simplifying complex systems is critical to us at Workiva. Can you talk about your aspirations for Upwork's accounting and finance office with respect to technology and streamlining processes? 

A: When I joined Upwork five and a half years ago, we did not close a book. Just to be fair, that was one year after two companies—Elance and oDesk—merged. When the merger happened, of course, everything is going to be missed. So I started off with a team at ground zero, no monthly close. 

Now my team closes the books on business day four, and we publish the executive financial package on business day eight. We have an aggressive goal that by the end of 2024, my team is committed to closing the book on business day two, if it's not business day one. I'm not coming up with this huge reduction of the business cycle just because of my ego. The reason why this is important is that the executive team needs to get the real-time financial results so that they can change direction or invest in the right place. 

Q: Where do accounting and debt management come into this, including technological advances such as platform partners? 

A: As you may have seen, we recently raised a half billion shares of convertible debts. In a typical convertible debt process, it takes a few weeks to one month, in some cases two months. One Sunday, I got a text from my boss, who is a CFO. He told me, “Junko, we're going to raise a half-billion through convertible debts.” So I said, “Great. I'm so excited.” And he said, "Oh, by the way, we need to do it within a few weeks." So my answer was, "No, it's impossible." Monday comes, he called me and he said, “I've got to tell you this. I just found out we need to file with the SEC next Wednesday, which is eight business days.” Crazy, right? But, you know, we really had this focus on how to get there and we made it. My point is, you have to have a great system. Oh, by the way, we used Workiva for our SEC filing.

Q: How was Upwork able to move so quickly and meet its aggressive goals?

A: Having the right people for the right position and the right system is extremely important because you never know what's going to hit your desk. That was really a testament to Workiva and also my teams. The legal team, the cross-functional team, we worked day and night. It's an incredible story that we could get it done within eight days.

Q: What does the future of automation look like for accounting and finance professionals from your perspective? What's the biggest area of opportunity as you see it? 

A: People may say I'm crazy, but I think, one day, bots or machines are going to close the books. I think the time will come. Until then, my focus has been to put in the right system, and we have done that. But system to system talking and eliminating manual work is extremely important. Someone like me who has been around for 25 years, I constantly remind myself that I need to be open minded.

For more insights from finance and accounting leaders, check out these other conversations from our Voices Amplified series:

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