How Stack Overflow raised millions while working remotely

According to CFO Jerry Raphael, attitudes of flexibility and empathy were key to the tech firm’s success in navigating a major funding round and subsequent strategy during the pandemic.
By Amanda Abrams

Editor's note: This article is part of the "Profiles in Productivity" series featuring insights from finance leaders across industries about the tools and techniques they used to motivate and lead their teams to productivity in 2020.

Like just about everyone else who sits behind a desk for 40 hours a week, Stack Overflow's employees have been working remotely since March. But unlike most other workers, the company's team managed to raise $85 million in investor funding during that time, a Herculean feat led in part by the tech company's CFO, Jerry Raphael, CPA.

"That was really challenging," acknowledged Raphael, who added that the funding round was followed by an intense period of strategic planning to determine how to use the capital, also completed virtually.

But throughout those grueling months, Raphael was always cognizant of the potential for videoconference overload and burnout among his colleagues. In an effort to coax the best work out of them, he tried to be as flexible and empathetic as possible, allowing his team to determine for themselves what they needed.

"Everyone is dealing with different things because of the pandemic," he pointed out. "The flexibility, that's the key."

Building trust without meeting in person

Among the top 50 most-visited websites on the internet, Stack Overflow began as a question-and-answer site where software developers could troubleshoot with one another. But in 2018, the company developed a separate product, an application called Stack Overflow for Teams, that allows businesses to communicate internally about code development, much of it privately, using the same engine.

The Stack Overflow for Teams app has done very well, particularly during the COVID-19 pandemic; its revenue has doubled every year since launching, according to the company.  

As a result of that success, there has been increasing interest among venture capitalists and other investors in the company, which has about 300 employees spread among its New York, London, Munich, and Austin, Texas, offices. So, in March, it launched a Series E funding round to raise capital, its first in five years.  

Raising money through a funding round can be exhausting even in the best of times. It involves creating and pitching a list of potential investors, while also developing a narrative and the data to back it up and explain why the company is a good bet. And that's just the first phase. After that, the process requires much back-and-forth as investors engage in due diligence and ask probing questions that need to be answered quickly and in detail. Much of that process is the purview of a company's CFO and the finance team.

Usually, most of that work takes place in person. "Normally when you raise money, you do it in the office, in conference rooms, over dinner and lunch. Venture capitalists and private equity, they want to get to know the people that are doing the work," explained Raphael. "It's extremely difficult to build a relationship and the trust in order to give someone $85 million over Zoom."

Raphael, who's been with the company for five years, has done this twice before. Prior to this position, he spent 10 years at Grant Thornton, then worked for a couple of other companies, including one tech firm.

This time, he said, was the most difficult. In lieu of the relationships that develop over months of in-person meetings, Stack Overflow wound up relying heavily on data and evaluations provided by Raphael and his colleagues.

"My team did the prep work for what we presented in the various meetings. We laid out the case for [potential investors] over several meetings until they felt comfortable. I do think there was a certain level of additional analysis we had to do to get people there," said Raphael. "Then they did a thorough vetting of our numbers, sales process, and plans — they looked under the hood very deeply."

On his 15-member finance team, only three had been through a funding round before. Nonetheless, Raphael said, "they really focused and put their heads down to do what they had to do."

The process was relatively tame until the last three weeks, when they had to simultaneously pitch the investment firms' most senior leaders and answer questions in the due diligence audit. "That's when everything came together."

In July, four months after the process began, Stack Overflow closed the round with $85 million in investment commitments from GIC, which is the Singapore government's wealth fund, as well as San Francisco private equity firm Silver Lake Waterman and several other longtime investors.  

"For a company of our size in the industry, $85 million is a tremendous amount of money. We can do a ton with it," he said.

Supporting staff with asynchronous work options

The end of the funding round didn't mean that Raphael and his team were off the hook. The next step came quickly: an eight-week strategic planning and budgeting process to determine how to follow through on the promises Stack Overflow's leaders had made during the fundraising phase. It was a big collaborative process run by Raphael that brought together representatives from all of the company's functional departments.

Like funding rounds, strategic planning typically occurs in person — in conference rooms over lunch and dinner, for example — but in this case it had to be done virtually.

When the shutdown started in March, Raphael had initiated 15-minute check-in calls among his staff every morning, as well as "meetingless Mondays."

Both were efforts to cut down on the number of emails and Zoom calls that distracted employees from the deeper, more focused work that was demanded of them. The approach also allowed staff members with more complicated home situations — children learning from home, roommates, or sick family members, for example — to work at the times most convenient for them.

But for the strategic planning effort, Raphael aimed to be particularly intentional about how he communicated with staff involved in the process. "With multiple scheduled meetings, it's fatigue," he said — and he and his colleagues had an eight-week marathon to get through.

In response, Raphael provided as many opportunities for asynchronous work as possible. Before the process began, he outlined what the company would accomplish during each week of the process. And at the end of each week, he sent out an email recapping what had been done, tasks that remained, and outstanding issues.  

"You get it when it's convenient to you. You read it over the weekend, or use meetingless Monday and do it then," said Raphael of his status update emails. Then staff members — representatives from marketing, sales, or product development, who were dedicating eight to 10 hours of weekly work time to the committee — would respond in writing with their contributions. If a sticking point arose, Raphael would convene a meeting if necessary.

Ultimately, he said, "it's about flexibility, meeting people where they are, giving them other options."

And he has continued that approach, even after presenting the final strategic plan to Stack Overflow's board of directors at the end of October (over Zoom, of course).

"Having the most empathy to meet people where they are and allow them the time to get things done, I find that the most helpful," he said. After all, many team members' lives are still upside down because of the pandemic.

"It pays back tremendously in terms of productivity. People are doing the work. If I said it had to get done in the 9-to-5 workday, I don't think we'd have the type of productivity we have today."

Amanda Abrams is a freelance writer based in North Carolina. To comment on this article or to suggest an idea for another article, contact Drew Adamek, a JofA senior editor, at

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