Written by Sarah Evans with thanks to Ruthie Nachmany, Aidan Feldman, Hendrick Townley and the rest of the Tech Mayor Project.

I volunteer as a Medicare counselor at the Health Insurance Information, Counseling, and Assistance Program (HIICAP) office in the NYC Department for the Aging. We answer questions about Medicare, offer impartial information about available plans, and help people find and apply for needs-based state programs that reduce medical premiums and costs. There are 8 full-time staff and 5-10 volunteers taking calls on any given day.
The staff at HIICAP are extraordinary. They have dedicated themselves to helping New Yorkers receiving Medicare access health care, and they have built deep expertise in a domain that is notoriously complex and often demoralizing.
And yet, every day these highly skilled, deeply committed public servants spend hours doing data entry, message transcription, and other tasks that are routinely automated in other sectors.
This is not a failure of anyone in HIICAP or the Department for the Aging - they’re given Windows 10 computers, some of which regularly fail to boot up correctly. They’re on locked-down, outdated systems with no ready access to developers. They do an extraordinary job given what they’re working with.
The Problem: Manual Work That Shouldn’t Exist
Every time a volunteer takes a call, we fill out a three-page PDF describing the caller and the substance of the conversation. We then email that PDF to HIICAP staff. Staff members read the document and manually enter selected fields into the system of record used to track call statistics that are then used to substantiate our claim to state funding.
This is not a marginal task. It consumes hours every day.
The consequences are immediate and concrete. During enrollment seasons, we do not have enough capacity to return calls from everyone who leaves a message. Some of these people may not get the help they need to enroll in insurance before critical deadlines. The office does not have sufficient staff time to develop materials or train volunteers on cases involving both Medicare and Medicaid—a category that is common, high-stakes, and brutally complex. If someone has a Medicaid-related issue, our policy is to direct them to the HRA helpline or an assisted enroller, where it can take a long time to reach a person. These are just the obvious effects - if they had the bandwidth, I'm sure the staff at HIICAP have a long list of creative outreach ideas that could have incredible impact.
This is the situation in an extraordinarily functional office. HIICAP exceeds state and national standards and, ultimately, delivers a very high quality service to New Yorkers. This is not a story about underperformance, but underutilization: with better tools, the excellence of HIICAP staff could reach more people.
Every unreturned call, every person with a complex case involving Medicaid redirected to another call line is an avoidable injustice that’s a direct result of poor software.
Why This Is a Justice Issue
It is wrong to waste skilled public servants on unnecessary work. This is not just disrespectful of their service. It’s not a morally neutral inefficiency - it hurts people.
The people who fall through the cracks are not random. They are people who rely on both Medicare and Medicaid. People who have trouble making phone calls and never get around to calling back. People who work during business hours and leave a message at 5pm in the last week of enrollment season. One of the laws of physics in government is that when resources are scarce, access goes first to the people who have the time and skills to pursue the help they want.
When civil servants are given outdated tools - or no tools at all - they accomplish less than they would with good tools. And when amazing civil servants are hobbled with difficult workflows, even if they still manage through sheer grit to do 95% of what they’d be able to do otherwise, that 5% of calls that don’t get returned always contains some of the most vulnerable people.
The Technical Reality
From a technical perspective, what HIICAP needs is not complicated. The underlying technical challenges are well understood and widely addressed in other sectors. Data entry, message transcription, and scheduling are largely solved problems from a technical perspective.
The problem here is not technical. The problem is budget, internal capacity, and will.
Without strong internal NYC digital service teams, improving tools would require writing a detailed requirements document, securing funding, and contracting the work out. Without an iterative improvement process, what a contractor would deliver would likely be expensive and incomplete.
Given the current constraints of NYC’s technical capacity, continuing to do this work manually is a rational choice.
A Systemic Failure
What I see at HIICAP is not unique. I hear similar stories across city and state government. People who care deeply about health care access, homelessness, or food insecurity dedicate their lives to public service - and over and over, they find themselves stuck doing data entry or working around broken software. In some cases, agencies are still using paper.
The effects are visible everywhere.
- HRA application processing is delayed by difficult-to-use software.
- The Fire Department is unable to consistently enforce code violations because they’re working with incomplete software delivered by contractors.
- NYC’s Payroll and Pension processing system is 40 years old, and 40% of the people managing and operating it are immediately eligible to retire. Government contractors and new civil servants warn each other to expect months of delay before receiving their first paycheck.
- Only 30% of respondents using Archibus, a new system built by contractors to track DCAS work orders, said the data was reliably accurate.
These failures are not isolated. They are the predictable result of chronic underinvestment in internal technical capacity.
Building Is a Political Choice
We need political clarity when it comes to technology. We can oppose tech oligarchs, exploitative platforms, and products that entrench bias and inequality without rejecting technology itself. If we want a government that reaches everyone, especially the most vulnerable, we need to embrace responsibly implemented technology in government. Building internal technical capacity is one of the cheapest, fastest, most effective ways we have to unlock the latent capacity of the existing civil service.
We need good tools in the hands of the people who keep our city running. We can’t afford to continue to accept half-baked software from contractors who have no stake in long-term outcomes. We need strong digital service teams that partner with civil servants internally to build and refine tools that will free front-line workers to focus on the work they joined the civil service to do.
The quality of the tools we give civil servants determines the reach of public services. When those tools are outdated or missing, even the best civil servants can’t reach everyone.
Outdated technology in government is not a minor inconvenience or an abstract inefficiency. It is a justice issue.




