Since our last update, here are a few ways we have been making and measuring progress.

Ease of Reading

We have been using grade level readability as an important measure of success. Why? It can help measure if our content is easy to understand for everyone.

This measurement also relates to translation. Simpler, easier-to-understand content means higher-quality translations into other languages.

We used grade reading level analysis to measure the impact of our file a complaint page redesign. We found that the text went from a Grade 9 reading level before to a Grade 6 reading level afterwards.

👉 There are plenty of free tools you can use to measure the grade level readability of your own web content. We used Hemingway’s free online readability checker. Microsoft Word has a grade level readability checker too.

Ease of Navigation

We worked with our partners at the Illinois Department of Labor to try new visual designs for the accordion elements on the File a Workplace Complaint page.

Our new accordion elements give more visual space between text, making the list items easier to scan and navigate.

We worked with our partners to use their Content Management System’s Custom CSS feature to implement the new designs.

👉 This video walkthrough from the Illinois.gov WCM Authoring Guide shows how to use the Custom CSS feature.

Breaking Big Work into Smaller Pieces

Redesigning the File A Complaint page was a starting point for a larger redesign.

We tackle big projects like website redesigns by breaking them into smaller pieces. This is a core principle of agile software development. In our process, we call it “Build, Brick by Brick”.

We worked with our partners at the Department of Labor to assemble the different pieces of work into a high-level roadmap, and decided which parts of the site to redesign, piece by piece:

Using Personas

Our next area of work together focuses on the homepage. The homepage lets us take a broader look at the people who access important labor law and rights information. Who uses the website? What information and services do they need from it?

We used a design tool called user personas. We identified groups of users, and then summarized their needs into representative types. These personas help us think about the website from a user’s point of view, and help us figure out who we need to talk with for user research.

We especially want the website design to support users who are visiting the site for the first time, and may not know what they need.

Measuring Impact

How will we know if the next step of our work is successful?

We plan to look at:

• Grade level reading analysis — Is the new content easy to read and understand? We are aiming for a sixth grade reading level.

• Web analytics — These can help us understand how users are interacting with the homepage. We want to see a lower bounce rate, meaning fewer users visit and then leave the site without clicking links or taking further action.

• Semantic and accessible HTML — Semantic, accessible HTML is crucial to make sure that the page is accessible for people with disabilities, such as people accessing the site with a screen reader. Semantic HTML helps people find and share information easily, and helps search engines and AI tools accurately read content from the website.

• Qualitative feedback from user research — Do workers and employers find the redesigned page easier to use?

Stay tuned!

Thank yous

Thank you Cherita Ellens for suggesting we use grade level reading analysis to measure our work.

Thank you to Brian Boyer for advisory support on product roadmapping.

And thank you to our terrific partners at the Illinois Department of Labor!

About IL*DS

Illinois Digital Service is a nonprofit technology partner.

We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

To bring this vision to life, we partnered with Xchange Chicago, a first-of-its-kind onshore IT delivery model that embeds apprentices into live client work.

Andrew McCaskill joined our inaugural apprenticeship cohort. During his apprenticeship, Andrew collaborated with a cross-functional product team, contributed to regular development cycles, and experimented with AI code generation tools like Google Antigravity.

Andrew created this post as a capstone reflection on his experience.

My name is Andrew McCaskill. I trained in software engineering with Xchange Chicago before apprenticing with Illinois Digital Service.

Since then, I have transitioned into the role of Scrum Master, where I apply my technical foundation to facilitate agile workflows and empower development teams.

During my time with Illinois Digital Service:

• I learned how to bridge the gap between clean code, agile methodology, and public service. I dived deep into JavaScript, CSS, and web design, and I learned a new technology stack for building a website: Jekyll and the Liquid templating language. Over time, my focus shifted toward how these technical processes can be optimized through better team collaboration. Exploring how AI can optimize code for high-performing web pages taught me that technical efficiency is only half the battle; the other half is the process that brings those solutions to life.

• I was surprised that AI agents and tools like Anti-Gravity can so drastically streamline development. Seeing these tools sync with Figma through MCP servers showed how the right technology can help with the heavy lifting. As a Scrum Master, I see this as a game-changer for removing blockers—letting developers focus on solving complex problems rather than getting bogged down in repetitive tasks.

• One thing I’ll take away from my apprenticeship is the culture of mentorship. I am walking away with deep gratitude for the energy Alex, Emily, and Savannah brought to every meeting. Their willingness to coach and teach has been the most impactful part of my growth as a tech professional.

I plan to carry this spirit of mentorship into my Scrum leadership, ensuring that my teams feel as supported and coached as I did during my time here.

The way they facilitated weekly meetings and ensured their productivity, gave me a framework to extend to the team I am working with now.

About Xchange Chicago

Xchange Chicago delivers commercial IT services to corporations, redirecting a portion of the billions in outsourced IT spend to create training opportunities and local tech jobs while launching sustainable, community-based business enterprises.

About IL*DS

Illinois Digital Service is a nonprofit technology partner.

We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

As an internal project, it was a chance to put our own practices into action while being our own client.

Who it’s for

People who want to learn about IL*DS: potential government partners, civic technologists interested in getting involved, and the public.

IL*DS is a young organization. We needed a public home that explains who we are, what we do, and how to work with us.

What we did

1. Started small to build momentum: We kicked off in December 2025 with our Product Manager Nathalie Rayter putting together a Mural board to map content and structure. We scoped from an initial 8-page site map down to a 4-page MVP. In January, we deployed a v1, password-protected version of the site to test and get feedback on. Working together, we were able to get from rough ideas about content to a live site in 2 months.

2. Worked with those close to the problem: The full team, IL*DS directors, PM, designer, and civic tech apprentices, collaborated throughout. Together we established Git workflows so everyone could contribute code directly. We shifted our project management into GitHub projects, and created and followed QA processes for our work.

3. Tested with real people: We shared early versions for feedback from our network of government tech professionals, and iterated through February and March. We swapped images, updated content, and added in some fun illustrations referencing the state of Illinois.

4. Delivered early and often: Rather than waiting for a polished launch, we shipped a working version fast and kept improving. The site launched publicly in May and, like all things digital, continues to evolve.

Using AI to move quickly

Early on we talked about what tech stack we wanted to use for the project and quickly agreed on Jekyll, hosted in GitHub pages. We wanted to keep the project super simple and open. You can view the repository (and contribute!) here.

As a learning experience, the team delved into using AI code generation tools to assist in building the site.

Some AI generation tools missed the mark. Taking the Figma mockups into Figma Make, Figma’s code generation tool, resulted in a React site using Tailwind’s UI library; overkill for a site as lean as ours.

But after starting a boilerplate Jekyll instance, Claude Code worked really well to get us across the finish line. The first versions of generated code needed a lot of prompting to get polished and accessible, but ultimately utilizing AI got us from high-fidelity Figma mockups to a launched, coded website so fast.

Never done!

To get our MVP live and up and running quickly, we pared down some of our initial wish list items, but the beauty of making websites is that you can always keep changing and adding to them. Now that illinoisdigitalservice.org is live, we’re excited to continue enhancing it and share those updates with you.

Team credits

• Product Manager: Nathalie Rayter

• Designer: Savannah Million

• Civic Tech Apprentices: Andrew McCaskill and Paige Wilson-Coleman

• IL*DS Directors: Alex Soble and Emily Herrick

About IL*DS

Illinois Digital Service is a nonprofit technology partner.

We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

Across Illinois, people rely on digital services to access benefits, find information, and interact with government — whether accessing the safety net, housing, voting, or any of the many services we rely on government to provide.

When these services are difficult to use or outdated, they create barriers for the public. Building and improving them requires skilled technologists.

But hiring technologists in government can be surprisingly challenging. These are the people who design, build, and maintain digital services — including software engineers, UX and visual designers, product managers, and data analysts.

Hiring systems were not originally designed for these modern roles, and teams sometimes struggle to compete with private sector salaries.

I’ve spent over 13 years working in talent acquisition, including five years recruiting technologists for civic technology and digital service teams inside government.

During that time, I saw patterns emerge in what helps government teams successfully hire strong candidates.

Here are three lessons I learned from recruiting technologists for government teams.

1. Requiring a college degree will shrink your talent pool

Many job postings for technical roles require a computer science degree.

In practice, that requirement often excludes strong candidates.

Some of the best technologists are career changers. Others are self-taught or learned through certification programs or bootcamps. When recruiting for civic tech roles, some of the strongest candidates I saw had nontraditional backgrounds and learned their technical skills outside of a traditional computer science program.

These candidates often bring valuable transferable skills from previous careers.

Instead of focusing strictly on degrees, hiring teams should prioritize experience and demonstrated ability.

Removing unnecessary degree requirements can help expand candidate pools and create opportunities for talented people from a wide range of backgrounds.

2. Don’t assume certain candidates are out of reach

Government teams sometimes assume they can’t compete for certain technologists due to salary, background, or experience.

Sometimes that’s true. But not always.

In practice, I found that strong candidates come from a wide range of backgrounds, including startups, nonprofits, government, and the private sector. The bigger challenge is not where someone comes from, but whether teams unintentionally rule people out based on assumptions about compensation or motivation.

Many technologists reach a point in their careers where they are looking for something different. That might include:

• Mission-driven work

• Better work-life balance

• The opportunity to build technology that directly helps people

Government can offer all of that.

While it’s true that government roles can’t always match private sector salaries, compensation is not the only factor candidates consider. Many are motivated by meaningful work, stability, and the chance to have a direct impact on people’s lives.

The key is to position government roles for their full value, not just salary, including mission-driven work, work-life balance, and public impact, and to avoid narrowing your candidate pool based on assumptions about who will or will not be interested.

3. Don’t default to “no” in your hiring process

Government hiring systems can be complex, and it’s easy for teams to default to “no” when something doesn’t fit neatly into existing policies or classifications.

In practice, I saw this happen often. Even when working closely with HR, there were moments where policies were interpreted conservatively or not fully understood. This not only made it harder to move forward with strong candidates, but also limited teams’ ability to implement more modern, effective recruiting practices.

Modern technology roles do not always map cleanly to traditional government classifications. A software engineer, UX designer, data analyst, or product manager might be listed under a broad title like IT Specialist. Without flexibility in how roles are defined or communicated, teams can miss opportunities to hire the right people.

Teams that are successful take the time to understand how the system works and look for ways to make it work for them. Instead of stopping at “no,” they look for a path to “yes” to bring in candidates with the experience and abilities needed - even if it requires adjusting how a role is scoped, described, or classified.

Final thought

Government needs talented technologists now more than ever.

The good news is that many technologists want to work on meaningful public problems. With thoughtful hiring practices and a willingness to rethink traditional requirements, government teams can build strong, mission-driven technology teams that deliver better digital services.

And ultimately, that means better, more accessible services for the public.

About IL*DS

Illinois Digital Service is a nonprofit technology partner.

We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

In June 2025, we created a sign-up form to gauge interest in contributing.

We received more than 100 responses — what a signal! People want to show up, and put their skills to work making government services easier to use.

We are excited to launch the 2026 version of our Talent Network Form.

• If you submitted your info in 2025, we have it. No need to resubmit unless your interest or availability has changed.

• If you are learning about Illinois Digital Service for the first time and are interested in contributing, please fill out the form below:

🚀 Sign up for the Illinois Digital Service (IL*DS) Talent Network 🚀

If you sign up, we will use your contact info to reach out about volunteer and paid opportunities to support Illinois Digital Service projects as they arise.

Please feel free to share this form with anyone in your networks who may be interested. Thank you!

Thank you to Omar Gonzalez and Nathalie Rayter who helped design and develop the 2026 Talent Network form.

About IL*DS

Illinois Digital Service is a nonprofit technology partner.

We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

• onboarding three early-career civic technology apprentices

• building an Illinois Digital Service website

• partnering with the Illinois Department of Labor to improve the online “front door” for labor complaints

Read on for more!

Working with the Illinois Department of Labor

Illinois Digital Service has been working with the Illinois Department of Labor to improve the online “front door” for Illinoisans who need to file a labor complaint.

Who it’s for

This work focused on supporting workers whose labor rights were violated because their employer did not follow workplace laws—for example, by stealing wages, not paying minimum wage, or denying meal breaks.

Why

The Illinois Department of Labor (IDOL) is dedicated to enforcing state labor laws, helping employers comply with the law, and increasing public awareness of workplace protections.

IDOL wanted to improve their online presence and make their website friendlier to use. They started with a specific goal: Make it easier for workers to find and submit the right complaint form.

The Illinois Department of Labor noticed that workers experiencing labor rights violations were sometimes filling out the incorrect form on their website, adding extra time and confusion to filing a complaint. They predicted that helping people find the right forms could also save staff time and effort spent processing complaints.

We partnered with the Illinois Department of Labor to work on an improved online “front door” web page that workers use to file complaints.

What we did

1. Started small to build momentum: Rather than trying to redesign the entire IDOL website up front, we narrowed in on the file a complaint page as our initial scope.

2. Tested with real people: We spoke with worker advocates who support people facing labor issues and help them file complaints. We walked advocates through the existing web page, gathering their feedback on issues that can cause workers to struggle.

3. Worked with those close to the problem: We engaged Illinois Department of Labor staff to ensure the new webpage met their needs and was easy to implement. We talked to staff responsible for sorting and responding to complaints: learning when and why workers submitted the wrong complaint forms, and how staff help workers understand their rights and navigate the process.

4. Delivered value early and often: We also collaborated closely with the staff who manage the IDOL website. We used their existing tools and aimed to write as little custom code as possible in order to deliver value quickly.

Results

In 76 business days, we:

• Conducted user research with three workers rights advocates and three IDOL staff.

• Developed new content and visual designs based on what we learned.

• Finalized the content with IDOL leadership to make sure it met their needs.

• Worked with IDOL to publish the new page using existing web management tools.

Designing Worker-Centered Content

Understanding workers’ lived experience helped us write new plain-language content.

For example:

1. We heard that it’s important to set the right expectations up front, and set workers up for success by making sure they have documentation to support their complaint.
   
   So we wrote content to help workers understand the steps of the process, and how to prepare and submit a complaint:

   

2. We heard that heavy legal jargon and many form options can be overwhelming and hard to navigate.
   
   So we re-organized content to focus on the labor issues that workers may experience:

   

3. We heard that the step of creating an online account can be a barrier—especially when trust in government is low, and when the meaning and purpose of the account isn’t clear.
   
   So we wrote content to explain and give context about Illinois ID accounts:

View our work live on the IDOL website!

Never done!

We embraced imperfection in order to deliver value early.

In the visual designs we created, several of the visual features required custom CSS code to implement.

We worked with our IDOL partners and decided that these visual improvements were “nice to haves”, but not “must haves.” We wanted to incorporate them into the new page, but we didn’t want to wait on getting more worker-friendly content out the door.

It’s normal to want a perfect web page to serve your users, but the truth is that websites and web content are never perfect—and they are never fully done. They are constantly evolving as the needs and expectations of users change. The key is to keep listening to your users, and keep delivering improvements based on what you learn!

Acknowledgements

Contributors:

• Kaleigh Simmons, research and content design

• Emily Herrick, research and UX design

• Alex Soble, product and project management

Many thanks to our terrific partner team at the Illinois Department of Labor.

Get Involved

In our next update, we’ll share more on how to get involved with Illinois Digital Service, including a revamped sign-up form for civic technologists.

About IL*DS

Illinois Digital Service is a nonprofit technology partner. We help state and local government leaders wrestle with the hard work of reimagining public services.

Illinois Digital Service is a fiscally sponsored project of the Digital Harbor Foundation.

Note: If you received this Substack post via email, it’s because you signed up for updates from Illinois Digital Service through our Google Talent Form (or subscribed directly via Substack). If you don’t want to receive periodic updates, you can unsubscribe below.

👉 Come on down and join us! In this newsletter, we’ll share how we’ve been working towards those goals and how you can plug in.

Civic Tech Workshops

Where is the next generation of civic tech talent going to come from? Illinois Digital Service is invested in building pathways into our field.

We are partnering with Xchange Chicago to offer civic tech workshops as part of their grand opening. Xchange is a tech training and jobs center located in Chicago’s south side Grand Crossing neighborhood, connecting local talent with commercial growth and community impact.

Our goal: create opportunities for youth and adults to learn about how government technology relates to everyday life, and what a career in gov tech looks like.

We’re looking for 2-4 civic technologist community members to support us in facilitating these workshops, and share a bit about your own personal journey into civic tech.

This will be a paid opportunity. Participants will:

• Join one planning call week of November 10

• Attend and support two 2-hour workshops on November 20 (afternoon & evening, exact time TBD)

• Contribute to a short write up about your experience

👉 Please fill out this short form by the end of the day on Friday, November 7th, or earlier if you are interested in joining and contributing. Thank you!

Demystifying Guide

Back in July, we held an IL*DS Community Kick-Off.

We asked questions like:

What have your experiences been navigating tech/design/product hiring in Illinois state, county, and/or municipal government?

What we heard signaled a lack of familiarity with local processes and ecosystems. Nathalie Rayter and Omar Gonzalez decided to see what they could do about that. Since this summer, they have been conducting desk research, interviewing applicants, and surveying the landscape of public sector tech jobs in Illinois.

Here is the result — a short, practical guide:

📃 Demystifying Hiring in Illinois State and Local Government 📃

The goal? Help folks find and apply to technology-related roles at the state, county, and city levels in Illinois.

Please give Nathalie and Omar a round of applause and appreciation for their work. Diving into complex government processes and trying to explain them in a simple way is not easy!

👉 Join Nathalie and Omar as they share key learnings at a virtual share-out on Thursday, November 13, at 5:30pm; you can RSVP here. We are very excited to share this with our community!

Visual/UI designer

We don’t have an illinoisdigitalservice.org website yet. But we are working on one!

We are looking to bring on a contract designer to join the IL*DS crew as we stand up our website. We are looking for a Visual/UI designer who can help us:

• Refine the IL*DS visual design language and our existing brand assets

• Develop design mock-ups and wireframes

• Build out UI components in Figma

We’re looking to bring on this designer on a short term paid contract this winter, with flexibility around the holidays. We estimate this will be a 30 to 40 hour project at a rate of $100/hr.

👉 Is this gig for you? Please fill out this short form by November 21 or earlier.

Thank you!