Aug 02 2023
Public Safety

Q&A: CTO Michael Rupert Is Ready to Improve D.C.’s Customer Experience

The recently appointed interim CTO spoke with StateTech about his priorities as he steps into the new role, including making his city’s online services more useful and accessible.

In April, Washington, D.C., Mayor Muriel Bowser named Michael Rupert as her administration’s interim CTO. Rupert, who stepped into the role with almost a decade of experience at the city’s Office of the CTO, served previously as the office’s communications director and most recently as associate CTO for customer experience. At the time of his appointment, he hinted at a few of his top priorities and immediate next steps, such as developing new business portals, improving digital equity and redesigning

Now, two months in, Rupert continues to move those initiatives along, focusing on improving the overall customer experience for Washington. residents. He spoke with StateTech about his office’s efforts to make the city’s digital services more streamlined, useful and effective.

STATETECH: How will your experiences as communications director and associate CTO come into play in your new role?

RUPERT: Technologists are really good at creating technology, but not always great at explaining in plain language how to use it effectively and how it can make processes more efficient. Another big thing we’ve focused on over the past few years is improving the customer experience and creating better digital experiences for folks. Our No. 1 priority is showing people how to use the tools we give them to do their jobs.

Last year, we started the tech enablement team, which essentially trains people how to use certain technologies, and we listen to people’s challenges and recommend different products we have at an enterprise level. A lot of the job is communications, training, listening and just trying to improve things.

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STATETECH: Could you talk about your digital equity efforts?

RUPERT: There’s a chunk of our population that isn’t fully online and is missing the benefits of that, whether that’s not feeling isolated if you’re a senior, being able to apply quickly for social services benefits or getting automatic telehealth reminders.

During the pandemic, we paid for folks’ internet through our Tech Together program. Then, after the pandemic started winding down, the federal Affordable Connectivity Program came out, which covers the costs for essential internet services in eligible households. So, we did significant outreach through schools and social services, made phone calls, and sent mailers and texts. We’ve been told by the federal government that D.C. had the highest uptake of any major area in the Affordable Connectivity Program.

There are also some places where service isn’t very good. Through our Community Internet Program, we gave internet service providers free access to the roofs of our 380 government-owned buildings. Within 30 days, they were able to create mesh networks that provided minimum upload and download speeds of 200 megabits per second to 2,500 households. Now, that number is up to almost 10,000 households. We held a summit, and we had a lot of major internet service providers come in to see what our first partners are doing and brainstorm on what’s next.

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STATETECH: You identified the continued development of the new business licensing portal as a top priority. Where does development stand now?

RUPERT: As part of Mayor Bowser’s post-pandemic recovery efforts, we were tasked with making it as easy as possible to do business in the city. The process previously involved logging in to multiple systems to file corporate documents, business licenses or taxes. We worked with the involved agencies, figuring out the business processes and details and mapping those out.

In February, we launched the first version of the portal, and we released the fourth iteration in mid-May. After you get your license issued and you’re in business, you will now have a single dashboard that tells you when things are due and when your license needs to be renewed.

We also want to create portals for private citizens. As a parent, I’ve had to fill out plenty of permission slips for my kids with the same information every time. Wouldn’t it be great if you could just go and say, ‘Is this stuff all still true? OK, send it to the teacher.’ Also, wouldn’t it be great if you could see that your child has had a library book out for four months? We’re thinking through all of these different things and trying to be proactive.

Michael Rupert
Our No. 1 priority is showing people how to use the tools we give them to do their jobs.”

Michael Rupert Interim Chief Technology Officer, Washington, D.C.

STATETECH: You are undergoing a major redesign of the city’s main website. What’s the status of that project?

RUPERT: It’ll be the first major redesign in eight years. There are 90 official agency websites that we would like to consolidate into a single site, so you don’t have to remember 90 agency sites and acronyms. Ideally, you’d go to, search something like ‘Get a business license,’ and it takes you right to the licensing portal. That’s how good we want to get.

This redesign is unique. Things are moving so fast. Ideally, we’ll have a prototype by the end of this calendar year, and a significant portion of it done by the end of 2024.

We also want to continue to be leaders in open data, not just from a transparency standpoint but in terms of providing different types of APIs for businesses to use. Wouldn’t it be great if you could type your address into a search bar, and it would show you who your local commissioner is, what precinct you’re in, what crime looked like last year, pulling in all of these data sources so you get a full picture of what you’re looking for. We’re also experimenting with AI and how it could help with open data. The challenge with open data is that you still have to spend the time filtering through what you’re looking for. If AI could do that work for you, that would be great.

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STATETECH: How important is customer experience when it comes to these initiatives?

RUPERT: It’s the most important thing. The moment someone is frustrated with a digital service, they’re going to give up and call you or submit a ticket. That’s energy that doesn’t need to be spent, because if we design things correctly, they won’t have to do that. That’s why feedback is at the forefront of everything we’re doing lately, because we know it’s not going to be perfect from day one.

STATETECH: Aside from the initiatives we’ve discussed, do you have other immediate top priorities?

RUPERT: I’ve talked about the shiny projects and new things, but the No. 1 thing we have to do is make sure our basics work. We need to make sure that everyone gets paid on time, that our broadband and in-building access points are working well when students are taking annual tests, that officers’ computers are working in their cars, and that there are no mobile dead zones. We have to focus on continuing to modernize the basics.

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