Innovation and Impact: U.S. Digital Service through the Lens of Women Technologists | Jennifer Kramer, Digital Services Expert 

In this final installment of our blog series, Innovation and Impact: U.S. Digital Service through the Lens of Women Technologists, we spotlight some phenomenal women technologists at the forefront of transforming the U.S. Digital Services (USDS) – the government’s digital agency for technology and innovation. They share their expertise, leadership insight, and impact on shaping the nation’s digital landscape, representing diverse software engineers, data scientists, product managers, and UX designers who drive innovation within the U.S. government.

Each blog delves into their unique journeys, career paths, challenges faced, and the pivotal projects they’ve undertaken, and share insights into the dynamic intersection of technology and public service. 

Jennifer Kramer is a technologist, wife, mom, and transgender woman living in Austin, Texas. After a two-and-a-half-decade career as a tech entrepreneur, cloud computing developer experience lead, and Director of Data and Engineering in media and public transit spaces, she’s been in the U.S. Digital Service since December of 2022. At USDS, in addition to sharing her experiences and cultural insights, she’s been working to upgrade tools and improve data collection and sharing with agency projects. 

Jennifer, you have a diverse background in technology, from being a tech entrepreneur to now serving at the US Digital Service. Can you walk us through your journey? What inspired you to join USDS?

I’ve had a very roundabout career in tech. I started around the birth of the web and worked for myself and few friends as a partnership doing backend web development until 2010. I spent time at a really big company, Hewlett-Packard, working on their cloud offering and then leading the Data Engineering group at Vox Media. I’d heard about USDS soon after it formed through media coverage and thought they were doing amazing work. Vox, being headquartered in DC, had a lot of crossovers to the Civic Tech world, so I was exposed to USDS even more there. When I was leaving Vox, I looked into applying at USDS, but I got a really exciting opportunity to work in public transit data, and what can I say, I really love trains. After that job I knew I wanted to give my best effort at joining USDS, and the rest is history!

Here at USDS, I’ve gotten to work with the Small Business Administration on some really interesting ground discovery work relating to how their regional offices interface with small business owners over the entrepreneur’s journey. I was able to see their work in person, dig into their tools, and present leadership with a report on how best to mature their solutions. Day to day, I’ve done a lot of work on our own USDS tooling, which has involved updating and refactoring Python applications, implementing CI/CD solutions, and working with our IT team to set up Kubernetes workloads.

I lean a lot on my experience building and leading development on dozens of web apps from early in my career, as well as the time I spent in management helping unblock projects, rubber duck developers, and guide other site reliability engineers. Here at USDS, there’s often a blend of both. We have problems that we solve with code, but we also have challenges that have to be solved with people and processes.

Cybersecurity is a major concern today. In your role, how do you ensure the security of the tools and data you work with?

I work to reduce risk by removing unnecessary features or data. Simpler is almost always better as far as security goes. I’ve done a fair amount of work in previous roles with the European Union’s General Data Protection Regulation and California’s Consumer Privacy Act and advertising data centered around browsers. Most of the projects I work on now aren’t as complex as that, but many of them have much more sensitive data. Ensuring that systems don’t have data they don’t need -saves a lot of headaches. You can’t leak information you don’t have or unwittingly share information you don’t have access to. Security is also something you have to create a process around. A system that you thought was secure yesterday can be insecure tomorrow by releasing a tiny vulnerability in a random dependency. Inevitably, the software that we build lasts way longer than we expect.

You’ve shifted between roles and company sizes throughout your career. Can you discuss the challenges and advantages of transitioning between small startups and larger organizations?

Throughout my career, I’ve worked as a sole proprietor in a partnership for a Fortune 10, a 1,500-person unicorn startup, a 100-person startup, a 0-employee seed round startup, and the federal government. I’m still wary, after 25 years of doing this, of coming into any environment thinking I know the answer to any of their problems. Organizations work the way they do for reasons, and while not all of the reasons are good, it takes time to learn which ones are helpful and which ones are true dysfunction and need to be addressed. Keep your eyes open, take cues from others, and find people you can converse honestly. 

A small startup or a new initiative is going to give the people in it a lot of freedom to make decisions and move fast. On the other hand, it can take longer to navigate the approvals structure in a large organization than to do the work itself. A startup can be great when you’re young and don’t have many responsibilities and want to get experience fast, but a large organization can be great when you’re a little further along in your career, maybe with kids and you need some stability, good benefits, and a bit flexibility.

In general, I’ve found I’m personally best suited for a sweet spot when organizations are young or small where the initial systems that got the organization that far have started to fail and new things need to be tried. In environments like that someone with some experience and confidence who can say “let’s try this” and uses their own political capital to do so can unblock a lot of dysfunctions. This is often what we do for other agencies at USDS. There’s another phase where organizations have moved beyond that and need to optimize their processes, which is a great time for some other kinds of folks is absolutely not where my gifts lie. Make sure you’re in an organization and position that needs what you have to offer.

Being transgender in tech undoubtedly presents its own unique experiences. Can you share some of the challenges you’ve faced and how you’ve navigated them? How has the tech community’s understanding and acceptance of trans issues evolved over the years?

It’s hard to know which and how much of you should show up in any particular space. I’m an adopted, third culture, neurodivergent, transgender, wife and mom of two who grew up with missionary parents. In a lot of meetings, just being the woman in the room can be a whole job. In some places it’s important to bring more of yourself so that other people can feel safe to share more of themselves. Vulnerability begets vulnerability, and acceptance begets acceptance. I’ve been in Women’s Employee Resource Groups and felt I specifically shouldn’t take up as much space sharing my trauma, but rather should focus on using my privilege to make sure other underrepresented identities are welcome and respected. Kind of like a queer mom, I suppose.

Being a very unique person and having the privilege to be visible can be an amazing gift. Having employees and co-workers tell me that I helped in some little way to give them the confidence to share and be their true selves means the world to me. It can also be very isolating and lonely. Don’t fall into the trap of getting tired and drifting away from your people, that just leads to further burnout. Let your peeps lift you up.

Queer and trans folks have been at the edge of tech innovations for as long as there has been tech, and what that hasn’t really protected us from societal pressures, it has created a space that’s more welcoming. There are still lots of places where transitioning will cost you a promotion, opportunities, or even your job (on top of potentially losing your friends and family). I think more tech companies understand that the queer, neurodivergent, gender-diverse folks down in engineering are often the ones who create the amazing new thing, and stifling that uniqueness and creativity is bad for business.

From your personal and professional experience, how has diversity in tech changed over the years? Why is it important to promote diversity in tech? What initiatives have you participated in or led to support diversity?

It’s improved drastically, and I think a lot of that is due to both awareness and the advocacy work done by organizations like Women Who Code (WWC) and PyLadies (which my wife was really involved in), and the democratization of tools. Back in the early 2000s I feel like web development was very much a boys club, and getting some impossible tool to work was considered a badge of honor. It took quite a few years of really difficult advocacy work and iterative tool maturity, but I think you can see that happening around 2011 with the founding of organizations like WWC and PyLadies. The tools were starting to be designed for humans to use and there was more, better documentation, which meant less gatekeeping for people who wanted to learn them. You could also do a lot more on the web and in tech without hitting those gates, and there were more software developers who didn’t look like the stereotypical computer science student.

You can see that as the web changed and technology became more accessible, things got a lot more interesting, which is something that ties directly to diversity. When your team is full of people who all have the same experience or face the same challenges, you only get one kind of myopic solution. When you have a team with different voices on it, and those voices are listened to, you build much better and more helpful products. Also, as you make an effort to increase and understand diverse perspectives, it can really shed a light on things you didn’t even realize were problems, like the fact that the neurodiverse people or parents or remote workers were really struggling with some policy or process you had. When you become more welcoming and supportive as a team, you become more welcoming and supportive for everyone.

My experience with diversity efforts really started when I was at HP, which is where I had my first opportunities to affect the careers of other people. I learned a lot about women in tech then, and with my wife at PyLadies, and tried to push those efforts even more at Vox through ensuring diverse candidate pools, pushing for flexible work arrangements, and updating our career ladder to give more opportunities for advancement above senior. At the last company I was at I was able to encourage opening up opportunities to internal candidates to give a path for increasing our engineering diversity, and I started up an Employee Resource Group for Neurodiverse folks and gave presentations on understanding ADHD.

What are you passionate about outside of work?

I have a weakness for personality-filled, weird, esoteric tech art and retro computers. Projects like the Berg’s Little Printer, robot companions like Mayfield Robotics’ Kuri, or my collection of 90’s era Macintosh and Silicon Graphics computers. I love smart, clever design. I love stories. I love to learn about people. I love to travel. We’ve gotten the family to 5 of the 7 continents so far. I grew up with old movies from the 40’s thru the 60’s, and really love that fashion and style. In that way, transitioning was life changing. I wore ill-fitting t-shirts and jeans or cargo pants every day for three decades and it was three decades too long. Vintage style, not vintage values! Last but definitely not least, I love being a wife and mom.

What advice would you give to individuals entering the tech field today, especially those from a historically marginalized and underrepresented group?

It can be really hard to figure out what you want out of your career, and it can change over time, but it’s a lot easier for people to help you when you have a target. People will often assume you want the same thing they want, and stereotypically for leaders in tech that can often mean being CTO or VP of Engineering. It’s rarer to find people who will honestly say they’d love a 30-hour week so they can be with their kids, or to find managers who will tell you that if your goal is to maximize your salary you need to be interviewing regularly and taking new jobs every 2-3 years early in your career.

Find mentors, and put in the time to be a good mentee. Their job isn’t to tell you what you need to know, your job is to figure out the right question they can answer or the right favor they can give. Treat them more like a doctor than a coach. Figure out what you have a passion for, or if you don’t have a passion for any of it and just want a good career. Tech is huge, you don’t have to chase the thing that everyone else is running after (*cough* AI *cough*). If you love organizing things and creating perfect little boxes for them, maybe you should look at infrastructure or compliance. If you want to build web applications, learn about the thing under what you already understand, like how HTTP works, how networking functions, or how multicast works. Forcing yourself to study what you think you should can be an exercise in frustration, but following your curiosity into a place you didn’t know existed can be a delight. Be pragmatic but avoid cynicism, especially if you find it growing in yourself. Life is too short to sit around doing work you hate.

Find your people and share your trials, tribulations, and wins. Don’t be afraid to ask for advice or help. Encourage and celebrate others. Learn how to ship stuff on time and give good estimates. Be like Geordi LaForge: underpromise and overdeliver. Be as dependable and transparent as possible; your managers will love you. Develop strong, loosely held opinions because managers can smell growth potential. If you’re in an unsupported situation and have tried your best to resolve it, don’t sit there wasting time. Give the person after you a hand up. Build good things with good people. Spend some time in civic tech, though probably not for the money. Fight for the users.