Amy Pitelka
‘There Was Never a Straight Path’: Amy Pitelka on Navigating Legal Barriers to Digital Transformation
| Amy Pitelka was Assistant General Counsel at OMB and USDS’s lawyer beginning in January 2016, later transitioning to Acting Deputy Administrator. Prior, she held legal roles at Dropbox and Google. |
Amy Pitelka joined the U.S. Digital Service as its first technology lawyer. She worked closely with the broader Office of Management and Budget to navigate legal barriers to digital transformation.
When Amy joined public service, she was startled to see how much power lawyers have compared to the private sector. Below, Amy discusses the importance of small victories; why critical work doesn’t necessarily have to be interesting work; and what USDS looked like during the 2017 presidential transition.
July 1, 2019
Kathy Pham:
Amy, when did you start and what was your first day like?
Amy Pitelka:
January of 2016. It was Snowmageddon, it was really cold, and I showed up in a suit. I met with some other folks who were starting at the White House and took an oath in front of a very large flag, and then stopped by Jackson Place. It was really exciting, very fun.
But my time with USDS started before then. The previous fall I had met Nicole Wong, who was consulting for Dropbox. Our Chief Information Security Officer (CISO) at Dropbox at the time went to work in White House security, and I didn’t really know what that meant. But I thought, “Oh, that sounds so cool.” Truly it had been a life ambition that I had lost track of. Meanwhile, Nicole had just come back from her tour with the Office of Science and Technology Policy (OSTP) and I asked, “Hey Nicole, how do I go do this?” She introduced me to Alex Macgillivray, who was at OSTP at the time and was previously the general counsel of Twitter. He said, “There’s this weird project over at the Department of Health and Human Services (HHS) where legal is blocking a critical part of open enrollment’s use of technology.”
I became a consultant for a law firm who was a consultant for a government contractor who was working for HHS. In about a week we figured out how to bridge the gap between understanding technology systems and legal compliance requirements. Folks had just been talking past each other. I thought, “We did this in a week? This is amazing. What an incredible experience.” I felt like I had such a huge impact so quickly.
But I also thought, “Where are all of the engineers?” I had coffee with Alex and he brought me over to USDS. I met Haley Van Dyck and Joe Crobak. I said, “I’ve been trying to find engineers for the last week. We literally had vendor sales people explaining to us how the system worked.” And Joe replied, “I’m right here.”
I thought, “This is amazing. I need to come back now that I know where the engineers are. We can get so much done.” I applied to USDS, but it wasn’t until I met Jennifer Anastasoff at a fundraiser that she said, “Oh, now I understand why your application makes sense. I’ll go tell people.” Two weeks later I got some interviews and it all moved very quickly.
Kathy:
This piece is really important to the story: Sometimes you don’t know what you don’t know. And in this case, it was the role of legal counsel inside USDS. What was the team like at the time you started?
Amy:
The team wasn’t really a coherent team. It was agency teams that came together once a week. People were very welcoming and had a sense of, “We’re all in this together,” which was enormously important to get through the battles we were fighting. But there were definitely factions inside USDS, and some folks who were not positive influences, and that was really disappointing. But that’s true everywhere. It always felt like there was more to be done than there was time, which was good.
Kathy:
How would you describe USDS?
Amy:
As an ad hoc cohort of individuals who all showed up to make an impact and a difference.
Kathy:
And what was your role when you started?
Amy:
I showed up and on day two realized that all of the laws that apply to the federal government are different from those that apply to the private sector. I had to basically learn a new jurisdiction. It was like, “Now go learn French law. Have fun.” But fortunately there was Snowmageddon, so I had three days holed up in my apartment. It was enough time to learn from various folks what the important laws were, and where I should start paying attention, like the Privacy Act and the Paperwork Reduction Act (PRA).
I got up to speed reasonably quickly. But the week after that, I was pulled into the office of the General Counsel of the Office of Management and Budget (OMB). It was Ilona Cohen at the time. She is such a badass. I hadn’t yet learned you should never go into a government meeting not knowing what’s going to happen.
Ilona said, “I hear that you’re a lawyer and you’re working at USDS. That’s great, but now you work for me.” I said, “Well, I guess I’ll go talk to Mikey about that.” It actually ended up working much better than our original intention. Moving into the General Counsel’s office empowered me to actually make decisions, and made me a part of the team of OMB lawyers — They were an incredibly smart group of folks who knew a heck of a lot more than I did about what we were trying to do, and together we could problem solve through most of the hurdles that the USDS team kept facing.
Emily:
Amy, when did that transition happen?
Amy:
It only took two to four weeks. The transition itself was scary, because I didn’t understand what was happening and I didn’t know what Ilona’s agenda was at the time. I had come in with the intention of helping USDS to achieve its mission, and was now worried about becoming a career government attorney. But it quickly became clear that Ilona and one of her political deputies were extremely invested in ensuring the success of USDS — in no small part because Andrew Mayock, who was Deputy Director of Management at OMB, had made it clear to them that was a priority. But also because they were serving for the same reasons the rest of us were: They really wanted to make the program the best that it could be.
There were pros and some cons of me being an OMB lawyer. The pro was that agency attorneys would say, “Okay, OMB blessed this, and so we are covered.” The con was a feeling of, “Why is OMB coming and messing in my sandbox?” Which is what USDS got everywhere we went: “Why is the White House coming in and screwing with our agency?”
Emily:
This was your first time in government. What was it like doing product work in government versus a product organization?
Amy:
The biggest difference was that when I advise technology companies, I am advising. I say, “Here’s what I think the law says. Here are some various paths forward. Here are your options and here’s what I advise you to do.” You have to really, really believe that a thing is illegal in order to block it in the private sector as in-house counsel. The ramifications have to be so bad that it could shut the company down — you’re going to have to pay a huge fine or people are going to go to jail.
In government the lawyers get to say yes or no, and that’s really rare in tech companies. We call it “throwing ourselves over the tracks.” The federal government is set up such that you can’t do anything that you don’t have the authority to do. That means the default is no.
Emily:
So in government, in addition to having to understand the law, you are also in charge of interpreting it to make decisions. The bar is set in a very different place than it is in the private sector.
Amy:
Yeah. And that’s not well enough understood. It was shocking to me that people who were supposedly in decision-making roles, who were bringing forth policy proposals, were on this legal tightrope and had to get the approval of the lawyers. Lawyers were way more powerful than I think even they understood. I don’t think the lawyers understood that they were decision makers in the way that they actually were.
Emily:
What did you spend your time on?
Amy:
It changed over time. For the first nine months, it was a lot of firefighting and then one main project. Our comms team was constantly trying to get any kind of communications out, whether it be mini articles or a video. This meant figuring out the review process for each of these items, and then helping to shepherd that through.
There was also a constant stream of questions from various project teams: “Hey, we heard this thing about this law. Is this true? Is this not true? How does this apply to this agency?” At the beginning I had no idea what the answer was, and so I had to figure it out. Part of that was normal legal research, and part of it was having conversations with other lawyers. Most of them were super helpful, but there was some turf war.
Ginny Hunt brought me in to work on this project for health eligibility enrollment verification, and using that technology for other social services. A bunch of lawyers at HHS said it was illegal for that piece of technology to be used for anything other than healthcare. I read the Affordable Care Act (ACA) and said, “What about this provision about using some stuff for these other things?”
After the first nine months, I started figuring it out. We started to see the issues that every single project team runs up against. I started thinking, “What are the laws, the regulations, or the policies that we would actually have to change in order to remove the fundamental structure of these barriers that we keep running into?”
Emily:
What were some of those barriers?
Amy:
The classic one is the Paperwork Reduction Act (PRA). Another huge piece was our interpretation of the Privacy Act, which was passed around the same time as the PRA, and required forms to be filled out by every project that weren’t applicable to modern technology. Those laws perpetuated the inclination to leave old systems in place, rather than making incremental improvements. This is a terrible way to build technology – the private sector iterates, but government was still launching entirely new systems every couple of decades.
Emily:
Was there any legal challenge, problem, or question you faced that you find especially interesting?
Amy:
So much of the legal challenge was a political challenge. Or, it wasn’t particularly interesting because it was intricate administrative law stuff — frankly, just boring attempts to make your way through all of the various policies that had been written over the past few decades. Most of the work I was doing was not interesting to most folks. It was just important.
Emily:
A lot of the work you did enabled everyone else to operate in the way they needed to. Did you see any turning points for USDS in that context?
Amy:
Yes, but they were small. Everything was really incremental. We worked for months and months trying to tweak an example exception in a memo about the PRA showing that certain technology practices were fine when the standard response USDS teams were getting out of agency counsel was: “Clearly, this isn’t allowed.” Yet we were delayed because people couldn’t agree on specific word choices.
We finally did get this example exception through, and I was really excited about it. Other folks felt really good about it, too: Mikey, Haley, Ilona. It was a small thing. But it depends on where you’re sitting. Did it repeal the PRA? No. Did it change the overall structure of the statute? No. But we had another example to convince agencies that the things we were doing were okay.
Kathy:
It’s hard for any one person to see everything. What seems important or what is a priority can be very different.
Amy:
It’s very true. I think a lot about the work I did shaping memos, especially toward the end of the Obama Administration when there was this huge push to try to get as much guidance out as was reasonable. We wanted to use that as an opportunity to clarify things and help USDS teams going forward.
Kathy:
What kind of guidance?
Amy:
So information didn’t come out that said, for example, “The cloud is illegal.” When the Trump Administration came in, it was actually an opportunity for significant impact. There weren’t many people around, so if you could convince the people who were there that you knew what you were talking about, then you could start restructuring organizations and moving guidance out much more quickly.
Emily:
When did your tenure at USDS end? Were you there through the transition?
Amy Barker:
It ended in June of 2017. I stayed through the transition, given that so many other folks were leaving. I was looped into the work Ginny Hunt and Haley were doing and found it enormously rewarding. Then I became the USDS Acting Deputy Administrator for a month while Matt Cutts was figuring out his long-term number two.
Emily:
You mentioned all of the opportunities for progress and for change during the transition. Did any of them happen?
Amy:
That’s a great question. I don’t really know. We got a couple of Executive Orders through that really prioritized technology transformation. And the thing that I was most proud of, and most hopeful about when I left was a weekly Roosevelt Room meeting on key issues that had become an extreme White House priority. We were meeting in the White House every week with this pretty senior person, and Jared Kushner would come by every once in a while. It was cross agency in a way that was not ad hoc. And I had not previously seen that outside of the national security world.
Emily:
What were some of the priorities in those meetings?
Amy:
We had strategic objectives. They included cloud services adoption, collaboration tools, and Trusted Internet Connections (TICs). Basically, the government approach to security. The idea was that if we had the ability to use ordinary technologies that the private sector leveraged daily across all of these agencies, we could communicate in a way that was totally impossible. It was like, “We need to move into the modern collaboration era.” IT investment reporting, procurement, budget, PRA, and shared services were all also on the agenda. And the Privacy Act with its constant Computer Matching Agreements.
Kathy:
Can you share what else you’re really proud of or left a lasting impact?
Amy:
When I came back to help the Biden Administration in 2021, I discovered that the HHS General Counsel memo resulting from our work on leveraging the HealthCare.gov backbone for other social services still existed and still gave the team the legal cover it needed to move forward in some critical areas. We had to pull it out and dust it off, but it showed how each of us could contribute building blocks for the next cohort of government servants to move a little more quickly towards efficient and effective modernization.