A government contractor crosses over to USDS

Steve Kelman reports on what prompted Kelly O'Connor to take an rather unusual career turn.

USDS

Recently I was working on a blog on the spread of civic tech. One of the people discussed in the blog was Kelly O'Connor, who, I discovered, had come to the U.S. Digital Service three years ago from the government contracting community. O'Connor spent eight years working at Deloitte, followed by a year at Gartner and four years at a small startup she founded with other Deloitte consultants. It struck me that the common paths into USDS were previous work in the commercial tech industry ("Silicon Valley") and to a lesser extent government itself. I had never heard of a USDSer who came to the organization from a government contractor.

O'Connor confirmed to me she didn't know anyone else in this situation, but acting USDS Administrator Matt Cutts told me this does occur, albeit quite rarely. So I decided I wanted to learn more. Why might a government contractor employee move over to USDS? And what are the differences between life as a government contractor and life as a USDSer, given that in both cases the person is working on government IT?

O'Connor agreed to talk, and here is what I learned about her story.

She started at Deloitte right out of business school, just as Deloitte was launching its government practice in the wake of 9/11. She had worked as a school teacher before going to business school, and decided to sign up for the new government practice.

O'Connor mostly enjoyed her time at Deloitte, leaving after eight years because she wasn't turned on enough by sales to want to put in the time needed to make partner. But two things bothered her. One was that at Deloitte she was not in a position to "hack the bureaucracy," the phrase civic tech folks use to mean influence how the bureaucracy works. Contractors, certainly at her level, were not allowed to work intimately with government decision-makers.

A related problem was how Deloitte and other contractors did business with the government. As an example of her frustrations, she mentioned voluminous requirements documents the company developed for the government, which involved endless time and meetings, and typically ended up hardly being used. Related to that was slavish adherence to the government's performance work statement, even when a detour would have been much better given how things were working out. "We would keep working off the original PWS, no matter what," O'Connor recalled. "These same kinds of problems arose again and again: I felt it was like Groundhog Day."

One day, O'Connor said, she read a New York Times article about the newly named secretary of Veterans Affairs, Bob McDonald, and "what he was doing at VA with innovation, leadership, making services veteran-focused, improving VA websites, all of it. I knew he'd been CEO at Proctor and Gamble so I was really excited to see his approach." She was particularly interested in the VA because her dad had been a Vietnam combat veteran and bronze star recipient. Her first move was to apply for VA jobs off the USAJobs website. But despite her business degree and contractor experience, she never got contacted.

O'Connor also "hounded my entire LinkedIn network at VA," she said. Through a link to a link she got in touch with Marina Martin, VA's CTO and chief honcho for USDS at the VA. Within two weeks, she was hired. Then, not long after O'Connor arrived, Martin invited her to join regular briefings with Secretary McDonald, a major experience for her because it was so different from her level of access to decision-makers at Deloitte.

O'Connor begun learning how USDS did business starting her first day on the job, and it was very different from what she had been used to as a government contractor. "The first shock was the tools -- I had never used Github and Slack before," she said. "I was used to Sharepoint and email. Everything at USDS was faster and more fluid -- I soon found I was spending a quarter of the time on email compared to what I had been spending before."

Beyond the tools were the techniques. "I started learning about sprints, mockups, and minimum viable products, all that was new to me," she said, but above all it was "awesome to watch designers and engineers work with rapid prototyping, peer review of each others' work, and collaboration. It was like watching a symphony being performed."

O'Connor also noted that the large government contractors have changed somewhat since she left Deloitte. "Most of the big vendors recognize things like agile, minimum viable products, and customer experience are important; you can see that in their marketing and proposals," she said. "But from what I've experienced in terms of seeing how that plays out on the ground with actual work, many teams are still doing a kind of 'agile-fall' delivery. One of the biggest gaps is on the user research work to define a minimum viable product, talking to real end users up front, and doing usability testing throughout the process."

During her first two years at USDS, O'Connor worked on rolling out a series of veteran-facing applications that were developed rapidly and iteratively using a minimum viable product approach. For the last year she has been working on cloud migration of VA apps and systems. On the cloud project, the role of the three USDS people is to provide technical advice and some engineering/development assistance to VA career staff.

In the three years she's been at USDS, the biggest change for the organization O'Connor has observed is that digital service team at the VA has moved from being a startup to a part of how the organization works. Compared to before, it is much more part of the larger fabric there. She believes the fact that USDS successfully transitioned from the Obama to the Trump administration convinced many career folks they were here to stay.

Originally O'Connor thought that, for financial reasons (she was taking a big salary hit at USDS), she would stay for only two years. But she liked the job so much that she renewed her term, though she says that beyond four years would not be economically feasible even if USDS allowed it. She has one year left.

"It's the best job I've ever had," O'Connor told me. And I am hoping some working for government contractors who are reading this blog post will be inspired by her example.

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