Making Government Work Better: Building Technology for Everyone with Rebecca Heywood

Hi everyone and welcome back to another episode of Sinking Up. Conversations at the intersection of tech, identity and innovation. Focusing on how LGBTQ+ professionals bring distinct perspectives to their fields. I'm your host Jake Tenenbaum. Today, I'm sitting down with Rebecca Haywood, founder and principal of Civic Works Studio, and tech jobs for Gov. Rebecca, welcome. Would you like to introduce yourself? Yeah, thanks Jake. I'm the founder and principal of Civic Works Studio, which is my own practice dedicated to improving how government deliver services for people. I work at the intersection of technology and government, helping governments and other organizations in the field tackle hard problems that are standing in the way of delivering better services and also helping technologists find their place in government and civic tech overall. I split my time between doing consulting work and running tech jobs for Gov, which is a platform, a newsletter and a coaching practice where I share jobs, news and analysis on tech and innovation in government. I'm going to ask you a question that people often ask me when do you sleep? When I can. Yeah, that's about right. It sounds like, especially the tech jobs for Gov, is a passion as well. Yeah, it really started as a passion project. It started as a side project back in 2022 when I was just seeing tech layoffs happening across the board, but it was a time when tech and government was really flourishing. The Biden administration was doing a lot of investment into what it looked like at the federal level. And we were seeing tech teams and digital teams in state and local government really take off. And no one was talking about it. It was outside of the government bubble. No one knew that there were jobs that doing really interesting work, paying decently well and allowing folks to really take a breather from the private sector tech world. And so I started sharing them on LinkedIn, just creating lists inspired by another friend who called herself a job fairy. And it's grown from there. It started from a series of LinkedIn posts to a LinkedIn newsletter. And now I run a sub stack and a job board dedicated to collating and bringing all these jobs together in one place and helping folks who are looking for a way to have impact, see that government can be a really great way to do that. You don't know this about me because I didn't mention it and you have no reason to. I'm very envious of how you set this up. Back in that 2021-2022 time period of life, I saw a lot of tech jobs closing in a way that wasn't quite what we have now. And I want to do my part. And so I made it a mission that every week or so, I would write a new LinkedIn post and ask people to submit to me job openings that they had or people who are looking, friends who are looking. And I would anonymize them and say, "Someone with these skills is looking at it." Or this friend at this company is hiring and trying to put those two together. And it was so time consuming and so hard to do just by collating information and then putting it into a LinkedIn post. Putting it into sub stack was like a much smarter idea. I was not at a time, like in a way to do that at that time. You saying this? I'm like, "Oh my that's what I wanted to do years ago." I mean, it took me probably two years before a year and a half before I put it in sub stack. Partially, I mean LinkedIn doesn't give you a lot of information. It doesn't give you a lot of control. No. Also kind of seeing what it could be. I mean, for a long time, it really was just sharing jobs, things people shared with me, things I saw, things I looked up because government job boards are terrible. They're all individual to a jurisdiction. The platforms generally are not great. And it's hard to find if you don't know that it's there, but the jobs can be interesting. I would just sit down and kind of dedicate four hours a week to it and hammer it out. And I think it was just seeing what that looks like and seeing people use it made me keep doing it. And then earlier this year, I was laid off, actually, and it was kind of the right time to see what it looked like to formalize and to really take it to the next level. And so that's what I've been doing, kind of setting up my own company and really being able to find a way how do you balance the public impact side of it, wanting to get people into these jobs that can have a really important impact and also my own sustainability, which is I think ever the question of building your own thing. That is the founders dilemma that we'll get into that. Hopefully you're talking about tech for a dove is just so reminiscent and the way you talk about it because you can feel the passion coming from you on that. For people meeting you for the very first time, how do you describe who you are and what you do? Yeah, that's a great question. I've had a lot of different jobs in this field over the years. And I think that through line through them, the kind of short and sweet version is I make government work better. That is kind of my guiding goal in my career and has really shaped what that looks like. And there's ways I tie it back to everything I do. This idea of then we can get into the specifics, which sometimes is when people's eyes glaze over a little bit. I spend a lot of time working on how we improve the plumbing of government, all the behind-the-scenes stuff that needs to be in place so that you can deliver good policy and good services. If you're talking about Kira New York, mom Donnie's platforms, whether you care about buses or affordable housing or any of the other myriad of things, those are all policy ideas that need operational implementation. And behind all of that are things like how you hire people to do jobs in government, how you buy things in government and the technology that enables it all. We live in a digital age. And so my focus is really on that side of things. How do we really think about making change there so that other people don't have to think about it. You can get on the bus, you can find an affordable apartment, you can do any of-- Things should just work. Things just work, yeah. And we're not there yet, but there's glimmers and there's things that are working there across the country, both here in New York, and then I also do a lot of work nationally as well. What I think is really important to also highlight is that it's not a lack of want and it's not a lack of technology that's out there, but there are budgetary constraints. There's also legal constraints, and there's a lot of data like you are doing within New York, 7, 8 people, that's a lot of data. And then if tourists are coming in and there's some precautions there when it comes to credit card processing across the board, there's so many different things that are around compliance. So it's not just as simple as, oh, there's a Marctec or there's a technology tool that exists to just simply do it. There's a lot of things that go with it. Yeah, I mean, one of the things that I think is so interesting about working government is that your market and your customer base is basically everyone. So the way that can a private sector company, you would say we're trying to sell to this group of people and you can exclude people, edge cases, people who have more complicated lives for whatever reason. You can't choose to do that in government. Those are often the people that you need to work the hardest to serve. And that's a huge challenge because when you think about somebody whose native language is English, who has higher education, who is making a comfortable salary, the way that you navigate things is quite different. You have regular cell phone service. You have internet at home. You have time, honestly. In most cases, you can pay someone to help you with something. Many people don't have that. And that's who, when you think about whether it's public benefits or affordable housing or the time spent on a subway, it's important for everyone. But if that's affecting your ability to feed your family or do something else, those start to be difficult moments of do you understand bureaucratic language? Have you had to move a lot in your paperwork? Isn't all in one place? Or you lost access to something because you lost access to your person's figure or your email account for a while or all of those things, everything's to factor authentication now. Do you have cell phone service to receive the code to be able to do it? And so you start thinking about how do you deliver services digitally while also then needing to deliver services sometimes over the telephone or in person. How do you mirror those experiences? How do you collect that data? How do you make sure that somebody knows how to navigate a webpage? Because honestly not everyone does and you need to serve all of those people. And so it makes for really interesting work. It makes for really interesting challenges. And then you build in kind of the checks and balances for better for worse that come with government. There's a lot that comes with oversight. There's a lot of rules that have been layered upon each other that were all put in place for good reason typically at one point in time. But it's hard to update things. It's hard to make decisions. I mean buying a SaaS product can take over a year sometimes in some governments because of outdated rules that are designed not to buy a subscription-based service. They're designed to buy a construction services to build a bridge or they're designed to buy pencils which on a regular contract that looks very different. And so folks are trying to keep up. There's a lot there. There's a lot that goes into it. But that's part of what for me makes it so interesting is that yeah you're really working for in most cases. Yeah everyone for the betterment of society of your community all of those types of things. And it's really rewarding. Very obvious. I think I've used that word a lot with you today. Working for improving the lives of others. There's a certain weight of your shoulder in a way that when you're like doing good you can feel good about the end of day. Those hard days are still because you're making a difference. That's why I volunteer and it's why I encourage a lot of people to volunteer because you may not get that in your everyday for profit job but you can get that same sort of feeling. I'm not trying to compare one you know nonprofit versus working for God but you're still being a mess allery but it's still doing good and that's a major part of life. Yeah and I think there's a lot of ways to do it. I mean the last organization I worked with is a nonprofit called US Digital Response which works with governments around the country on short-term projects to help take the first step towards digital modernization and things like that. And they work with volunteer technologists to staff a lot of those projects. And the idea really it came out of COVID. It came out of this time when government was really overwhelmed. Things needed to move quickly online and people had time. But the models continue to say how do you take folks who want to use their professional skills to do good dip a toe into what this type of work might look like and do an interesting project and see whether it's just for that project there's a lot of people who've chosen to change their career in some way because of those types of experiences. But we don't often have also a ton of opportunities to use professional skills in that way. I mean maybe build a website for a nonprofit but that's very different. These are how user researchers and product folks folks with tech talent and hiring experience who are helping a government hire their first product person or helping show them what user research is and at the same time working on a public benefits project or figuring out what a use case for AI maybe or all sorts of things it runs the gamut but there are orgs out there and other ones like data kind which works more with nonprofits and data scientists but yeah it's an interesting question of like how does that come into your life and what's the balance and how do you how do you bring it there I encourage folks to consider shifting your career but that's not right for everyone 100% real quick growing up did you always imagine yourself working in government and tech if not what kind of led you there now it was an interesting journey as a kid I really wanted to build bridges of the literal physical kind I was really interested in infrastructure I was really interested in kind of the built environment in the world around us I love cities and I was told when I was eight years old my parents were like someone who built bridges as a civil engineer and so that was a path I took that's what I studied in undergrad and I quickly also came to realize I really wanted to know how for just stood up and that was enough for me and I found I came into this world in an interesting manner I never thought I would do something in tech I'm the only person in my media family who's not worked for IBM I come from a family of folks from our first in tech and all of that that I do it was never my interest the early days of cloud and Watson all sorts of things I think it was because I always wanted to do something that impacted people and at the time I really didn't see that connection I didn't see what that looked like so I came into government actually through civil engineering I learned in college that people design cities and people who do that are urban planners and that kind of the intersection of urban planning and civil engineering is transportation and so I got really interested in transportation I worked in transportation went to grad school for transportation and urban planning and got a job here in New York City doing transit planning I'm working on public transportation how do you get people from point eight to point B is this core thing that impacts everybody and really enjoyed doing that care a lot about that field but came to realize in that work that the things that were hard about it weren't what does good transportation policy look like we know what that looks like it's how to get that done and the things that were standing in the way of getting that done were how do you hire good people how do you hire the right people in a really Byzantine system and how do you buy things I mean I kind of got radicalized I guess as in that way to really think about that when I started questioning why these things were so hard my colleagues who I respect deeply were really good at navigating the systems and had never really questioned why they took so long there is are trying to buy something to pilot they could only buy from like one company in Spain it was a new idea was a modular thing bus boarding islands me that a rubber big puzzle that's a whole other conversation but it took 18 months to get two of them and I didn't understand why and I wanted to change that and so I shifted I went from transportation into the operational side of things people thought it was crazy but then I started working I went to the agency that does all the administrative operational stuff and again worked on it folks are from New York civil service which is the backbone of how New York City and New York State hires figuring out how to modernize it but we couldn't get to the tech we couldn't touch anything about the information the website the data systems and that's when came back into this world of how do we impact these things behind the scenes that ultimately change how we build transit systems how we do anything how you pick up garbage how you keep rats from being on the street like all of these things are impacted by it it's a child never could have imagined it always wanted to live in New York City but just thought I would be designing things and living here not necessarily designing how the city works itself it's so funny because I think that there are so many comparisons to non-government work in that same respect where whether in retail or you're in auto you're in some other industry where you're looking and saying I'm working on this thing but ultimately and fundamentally I cannot make a difference because of this thing over here until that thing changes all of my work is it's it's putting lipstick on a pig right but the point being is that our society has become dependent on technology that it is the corner stone for how a lot of things get done commerce government transportation and utility is so much of it. And so. Yes, it's great to have a nice UI. Yes, it's nice to have a great email system and great marketing campaign or great accounting system. But until I talked up, we don't see that impact take shape. I think we're at the, and you can tell me I'm wrong here, but I think we're still very elementary into the modernization of our government until where it needs to be if we want to see the future we want to see. Yeah, and I think one thing that we're really seeing is that there's a lot of incremental changes and you can have a lot of impact with incremental change, but we also really need to think about how do you do change at scale? Because I mean, not just in government, this is true in finance and in other things. Like you mentioned, there are so many main systems that still exist that are aging out. We can't hire cobalt engineers though AI is actually getting very good at helping with legacy modernization. There's a whole community of folks working on that in the context of government, which is really helpful in that case because we don't have very many people who can do that. And it's also thinking about one of the challenges. Technology is moving really quickly. This is something that gets talked about a lot in government circles is how do you balance your duty to the public to make sure that their data is safe, to make sure that you're not doing undue harm or causing unintended consequences, while at the same time being able to keep up with the change and also regulate the change. That's something that state and local governments are now really thinking about for reasons we don't have to get into. But it's a huge challenge. And then it comes back to my question that I think about a lot and put people at the center of all of this. You cannot operate government without the people who can understand what's happening in the tech industry, understand what's happening in these other industries, help make informed decisions about what is in value, what is in good faith and providing value to the public who can build some of these things and how to think about what you should do outsource. All of that to me, a lot of this comes down to the public. But it is an interesting question. Also, there's a concept called digital sovereignty. This getting talked about a lot. I was at a conference in Europe on civic tech and gov tech earlier this year. And Europe in particular and other places outside of the US are really thinking about how dependent they are on American technology or Chinese technology. And how do you think about that in the context of sovereignty? And it's a really fascinating question that is starting to come up here as well in the US at the state and local level across the board as you think about what happens when AWS goes out or any of these other AI in particular. But when you think about the dependencies that are there and then how much power and control they have over public systems, there's a lot of conversation and really interesting conversation, important conversations about what should governments own and be building and building in-house versus outsourcing to folks whose motivation isn't the public good. And I think that's the difference of working in these sectors of like when you can't change something in the private sector, you think about the motivation for that change is often the bottom line. Are you going to be making a profit in government? It's a really complex set, but typically it is, does this benefit that people are trying to serve? And there's a lot of nuance that goes into that, but it makes these conversations and the purchase really important and really interesting. I can listen to you talk about this forever for the record. I think this is incredibly fascinating and really eye-opening. A lot of areas that we don't think about, we take for granted. Jewish timing, I am going to move us into a couple of other areas, but do know that I am deeply interested in so much of this. Digging into the LGBTQ side of Gov and Tech, you helped launch one of the first LGBTQ resource ERGs at NYC Department of Transportation. What inspired you to take that on? Yeah, that was a very organic process. I had taken on some leadership roles in kind of queer and LGBT organizations in grad school and found my community really important. I was new to New York when I moved to DOT and there was kind of an informal group of people. I'm lucky urban planning is a very queer field profession. I've noticed that because we like to organize and make things nice and pretty, it tends to do that. Yeah, I think some of it's some city, I mean, historically urban planning is like a white supremacist field. That's a whole other thing, but in this day and age, it's very queer and it's this mix of advocacy and you can make change in your community. You can make spaces feel safe. So it's a really great time. I came out in grad school and kind of immediately took on some of that leadership because it gave me some control over how I built my community and it made me feel like I had a job in being able to do that in a place and then identity I wasn't totally comfortable with, but I gained a lot from doing that. And when I got to DOT, it was again kind of this thing where there were some folks who would go out together occasionally and I got involved with that, but it was very informal and it was very kind of disconnected and it was very planner forward. And DOT is an agency of 6,000 people. Most of those people work in the field. They poor concrete, they draw the lines on the street, they run construction equipment, things like that. They paint the bridges. All sorts of really interesting jobs that many of us in this community probably haven't read out that much about or interacted with people in. And again, it came up. There was some question and I have a tendency of asking why not. Why haven't we done this? Have we asked? Have we done it? So yeah, it kind of came about naturally a little bit. We started organizing. We started telling people I created an email list as every great organization starts and gave people a time and a date, which is a lot of how I've approached community building is like let's just tell people where to meet. And we had a lot more folks come, really interesting folks who hadn't really been connected before. Things got forwarded along. It was word of mouth. I got approached by the DEI group because they had been thinking about starting ERGs for a little bit and didn't really know what that looked like. It was right after 2015. It was right after Oberkiff fell. Oberkiff fell. Thank you. And so there's a lot of interest in it. And we were able to get some support to be able to talk about it publicly to be able to bring folks together in a social manner to get DOT to support marching and pride. There weren't very many agencies that were doing that at that time. There was a lot around gender-neutral restrooms and some other things around that time that they suddenly came to us, this group of folks who were really going happy hours together after work and having these informal conversations to help inform what that looked like. But it became a really big deal because I just remember about a year and we had a big event with leadership, a kind of Q&A session, a panel, a lot of folks weren't in a position where they could meet the commissioner. They could do other things. And there was a time for questions. There was a time for some response. What does it mean to you to have this? And a woman who, I think, had been at the agency for over 30 years who worked in the field, got up and said, she'd been with her partner for, I think, longer than she'd been at the agency and she'd never been out at work until this all started. And it just became a really powerful moment for me on why social connection matters. But also, I realized it's the connection across. There's so many silos at work where at the sort of the type of organization you're in. I would call people to collaborate with them. I would call this woman to say, tell me more about how this works because it was impacting my project and it made my work better. And we're able to do some really interesting things, give people confidence in a safe space, but also improve how the agency was delivering across the board, which was really powerful. I think that's one of the first times someone has mentioned that kind of benefit of a cross-organizational year. and it's so true. You're building a network. I mean, ultimately, it's a network. And you're building that network across an entire organization here at Adobe. We have a Pride ERG that spans across the country and spans every different type of work that we do. So when you start building those types of connections and your internal ERG, you all of a sudden unlock a network that others don't have access to. And I said, you can start saying, well, I know someone in that department or I have access to this. It's a superpower that we unlock. Let me open ourselves up to that sort of community. And I am so glad you brought that up because no one really talks about that benefit of an ERG that's not just bringing queer people together and else BTQ plus people together and talking about current issues, but you're doing what you best can as a community. I think it's really beautiful that you can not only give answers and give honest opinions of what you think, but also build that sort of cross organizational department or network that's really exciting, you know. I think it also opens up well-intentioned people to at least go to folks who may not have the answer, but may have a broader network to be able to help get it. I mean, something like gender and neutral westrooms, we didn't have at the time anyone in our group who is openly trans. There are now, but we had folks in our own personal networks that we could ask and we could look to and hopefully do a better intentioned approach for the folks who come next. And also really think about it came up like, what does it look like? I mean, there was it led into actually a lot of conversations then intersecting with the work they were doing for women's history month and other things about what it meant to be female in field work and that intersection and that intersectional identities came up for the first time with some of these folks because I mean, it may be stereotypical, but a lot of women who've historically been in those types of jobs are queer in some way and have been historically. And that's that's a really interesting intersection that the agency hadn't ever thought about. It's like the Subaru Golan. Yeah, yeah. And so it just brings up all of these other pieces and it really also stemmed into how do you connect with other agencies? How do you connect across the board? I think there are definitely superpowers, intergenerational. I just remember there's this incredible woman who worked there, who also worked for the gay men's health crisis in the late 80s and shared a lot of stories, I think that a lot of us wouldn't be in spaces to connect intergenerational either. And so you get benefit in that way in learning about the history of New York and the history and people's experiences across gender race, sexuality, and all of those things that to me are invaluable. And I value and cherish so much that experience. And I'm so excited to see. I mean, that DOT has many energies now that the LGBT refugees still there. Other city agencies have also leaned into that idea, and there's new types of community and support for folks that I think are probably continuing to break down those barriers. And not for nothing, but ERGs are a creative for recruiting. So if we are looking at younger people to get involved in civil service work, it's a great way to make your openness known. Yeah. And that's something that whether or not people it's talking about, like that is a huge part of recruiting and bringing talent in. So love to see that. Quickly coming towards the end here, yes, but your time between consulting and helping people find careers in civic tech. What states you most about where the field is headed? There's just so much that remains to be done. Civic tech is a really broad field. It's a really broad term. To me, it's really how do you use tech for good? How do you center how we use tech and government around the people you're trying to serve? Human center design, user research, all of that is still pretty new in a lot of governments. I know it's old hat to a lot of people, but we're still early in bringing product models to government. We're still early in bringing user research and all of that into this type of work. And so there's so much opportunity to do that loudly and to do that quietly. So I'm excited to see, I mean, people were shocked when USPS could mail your COVID tests automatically to you. But that's an example of civic technologists. I know some of the folks who are working on that being able to make things seamless and make things easy. And I think that's really the goal we want to grow the umbrella. And we want to make it mainstream. The field of civic tech is only about 10 years. Old it's maybe 12 at this point. It really started around when healthcare.gov kind of failed spectacularly. And then a group of tech folks came in to fix it to make it work that US Digital Service, which unfortunately is no longer around. But at the federal level started because of that. So there's a lot of opportunity in every level of government across the country and every nonprofit across the country that receives the government contract or that collaborates with government to try to deliver. Even when we see kind of things we're less happy about like in my personal case like work requirements for Medicaid or SNAP. How do you do that in the way that has the least impact? And that's the easiest to navigate for the people that's impacting. There's a lot of folks working on that now in every state across the country. So we're at a place where if you want to do this work, our community is growing. There's opportunity just about everywhere. And it's really to me like how do we leapfrog a little bit so that we're not always 30 years behind or 20 years behind or 50 years behind. But also just how do we keep centering things around people? And how do we change the culture of government to be focused on that? Because there's a lot of really incredible people working in government who do the best with the knowledge they have, with the resources they have, who've been told that they have to do things one way. And they are open to change. They're open to doing it differently. A lot of them have tried to do it differently and don't know how to navigate the system. Yeah, I think that's what I'm most excited about. Is just seeing how we continue to drive forward and to follow the example of what's happening here in New York of what's happening in New Jersey with a really great innovation authority or in Colorado, just totally rethinking how they do information technology and building out like a full-scale product model in every state across the country is doing something. Arkansas has some really interesting jobs open right now, which is maybe a surprise to folks, but everyone's thinking about it. And yeah, it's a big field. Very cool. Rebecca, thank you so much for your time. I'm like I said, I could ask you a thousand more questions if we have the time. Is there anything else you want to impart before we say goodbye? I think if you're trying to find a way to have impact in your career and are feeling kind of unfulfilled about what your work may look like, a great place to think about having that impact is government. One resource of many is tech jobs for Gov and techjobsforgov.com, but I'm just encourage folks to keep your eyes open and really think about the issues you care about and how you can use again your professional skills and your experience to be involved and to make a difference. Thank you. Yeah, I'll make sure to put all that in the show now so people can click through and I will also be checking out the sub stack as well. I'm not looking for a job, but I'm really interested in how you did it. So, Rebecca, thank you so so much. This was incredible. I don't think I've ever spoken less on an episode. I just let you talk and I was just sitting here captivated. So thank you. Yeah, thanks, Jake. I'm glad to be here. And everyone else, thank you so much, and we'll see you on the next one. Bye.