WeWork's VP of Engineering on the Big Difference the Little Things Make

For Randy Shoup, the longtime engineering leader and veteran of Google and eBay, software development is a craft best practiced with enthusiasm.

By now, Randy Shoup knows the difference between "good enough" and "out of this world." Throughout his 25-year (and counting) Silicon Valley career, Shoup has taken on leadership roles at small startups as well as global giants like eBay and Google. He has seen both success and failure up close, and he has seen how, when things go sideways, a fervent commitment to crafting great software can right a team's wayward course. One thing that has become clear: Often the smallest details—incremental improvements and even attitude—can have tangible effects.

Shoup recalls a project to improve eBay's search engine ranking that his team undertook between 2010 and 2011. "We did it in continuously deployed incremental improvements, and we did it knowing that our success was going to be the business' success," Shoup says. "And it was. After a year, this work alone drove a 2 percent increase in eBay's overall revenue. That's $120 million right there."

His latest adventure is with WeWork, a global network of work spaces, where he serves as VP of engineering. We sat down with Shoup to get his take on how the pursuit of excellence in DevOps can boost a business' bottom line and bring out the best in its engineers.

Modern Software Factory Hub: What differentiates DevOps software engineers who think of themselves as digital creatives and craftspeople from other DevOps practitioners?

Randy Shoup: All developers should build good software with good engineering practices fostered by DevOps, with its premises that software developers should be involved in test-driven development, and that continuous delivery of smaller units of work reduces risk. The distinction lies in treating DevOps as a set of practices for engineering excellence versus thinking of DevOps as just a set of tools. The software engineers who think of themselves as craftspeople are part of that first camp.

MSF Hub: How does that attitude translate into better results?

Shoup: When you pursue excellence in engineering, you know that producing better products that provide better customer experiences matters to the organization, and you act accordingly. You feel that you're an important contributor to tangible business value. In fact, you'll find that companies that follow this idea—Google, where I once worked, or Amazon or Netflix—produce higher-quality software more rapidly than the average organization where DevOps is just a part of their engineering processes. And those companies where software engineers believe in the impact they can have on the business are 2.5 times [Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations] more likely than competitors to exceed goals on everything from productivity to market share.

We did [the eBay search engine ranking project] in continuously deployed incremental improvements, and we did it knowing that our success was going to be the business' success. And it was. After a year, this work alone drove a 2 percent increase in eBay's overall revenue. That's $120 million right there.
— Randy Shoup, VP of engineering, WeWork

MSF: How can leaders get their own teams to embrace their jobs with engineering excellence in mind?

Shoup: There are different maturity levels in organizations. Some haven't even begun the journey to DevOps, and maintain siloed approaches to software development. But there are things that companies can do to either create a DevOps organization where excellence in engineering is a guiding principle from the start, or to adapt an existing DevOps environment to that view.

Whenever you want to make a serious change to an organization, there has to be a combination of top-down and bottom-up execution. There may be a top-down set of goals outlining the need to develop better, more reliable and higher-performing software, but those goals can't be met unless leaders give their development teams space, resources, and permission to take risks—that's the bottom-up component. Developers have to feel comfortable trying something that may not work out the way they thought. If they're afraid to fail, they'll be afraid to succeed, too.

MSF: So allowing teams to fail actually sets them up to succeed?

Shoup: When things don't work, you review incidents and try to understand them as part of retrospective discussions; but those should be blameless postmortems. An open, transparent and blameless review gives everyone a chance to focus on learning and can immediately transform the culture. That's top-down leadership.

Without that top-down support, nobody really believes that the transformations that companies outline in top-down goals can happen. With it, the company is positioned to drive bottom-up support for excellence in engineering, too, because developers become motivated to innovate and produce work they know will matter to the business' success.

MSF: How are you approaching the job of infusing engineering excellence into WeWork?

Shoup: WeWork has been following DevOps practices with a focus on engineering excellence. So for my part, it's very much a matter of reinforcing the practices that are there rather than rapidly changing things. We're not perfect yet, but, fortunately, our baseline processes and the positive and passionate outlook that developers need to bring to their work are already in place.

Jennifer Zaino
By Jennifer Zaino | July 11, 2018

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