Three decades on, Makstman is now San Francisco's new Chief Information Officer, in charge of technology and policy for what is arguably America's most tech-savvy constituency. He stepped into the job running a $140 million department with more than 260 employees in July, and gave the Chronicle his first interview this August.
Makstman said his internship in Chicago introduced him to the positive impact that local governments can have on individual's life, especially immigrants like himself, or on other disadvantaged groups.
Now 45 years old, with curly salt-and-pepper hair and a close-cropped angular beard to match, Makstman is an experienced hand, serving since 2018 as the city's chief information security officer. In that job he worked to standardize the city's cyber incident response software across dozens of departments and draft the city's guidance on using artificial intelligence.
Hardening the city's cyber defenses was no easy feat, technically or politically, and it took about half a decade of convincing at a time when cities such as Oakland and critical infrastructure across the country from hospitals to airports are increasingly being held hostage by cyberattacks.
Makstman is admittedly less experienced in politics, which is more of an art than the science of zeroes and ones he is used to manipulating. Forging consensus and communicating his goals clearly will likely be among the biggest challenges he faces as he takes on the top tech job in a city whose disparate departments run as federated technical fiefdoms, some with aging infrastructure of their own. "Every department has their own IT team," and in many cases different and unique software, he said.
That structure will likely be Makstman's toughest assignment. His power to set policy, enforce standards and centralize procurement is limited to the portions of the city government he oversees, although the technology department does risk assessment on big tech contracts the city signs, and can negotiate citywide deals for applications like Salesforce and Microsoft.
But with no plans in the works to consolidate his control over all the city's technology, Makstman will need to use persuasion and arm-twisting over other parts of the government to establish common approaches to IT wherever possible.
Here are Makstman's top priorities in the top job, his view on using AI in city systems, and the biggest challenges he faces, including those floppy disks still used by the San Francisco Municipal Transportation Agency to run its trains.
Q: Why did you take this job?
"Despite not being born here or growing up here, I consider San Francisco and this city as special to me," Makstman told the Chronicle. "So I think the reason why I wanted this job is because I think I have a unique perspective versus some other folks who might be coming from outside of really having ties, deep ties into the city, caring about the future of the city at a very personal level," he said.
He is quick to talk about wanting to use technology to make a difference in the lives of disadvantaged San Franciscans, and to talk about his own immigrant experience informing how he wants to run the city's tech stack.
"I feel very strongly about the service aspect of the job," he said.
That includes previous stints as an information security analyst at one of the largest federal nuclear laboratories, and as the director of technology risk management with Kaiser Permanente . "And after nearly seven years with the city already I think I've got a good sense of where the challenges lie, but also, more importantly, how to get things done," Makstman said.
Q: What are your main priorities?
"Fueling digital transformation" for the departments his agency works with and oversees is among his top priorities, Makstman said. That means cutting down on the legacy technology that many departments still use, including antiquated coding languages and, yes, the floppy disks that Muni still uses to boot up its train lines each morning.
But Makstman was quick to point out that there are both technical and political roadblocks to accomplishing those goals. He said he hopes to use the backing of the mayor and the relationships he built as chief information officer to make those changes a reality.
In that previous role, "I had to build a relationship with every single department," in the city, including the 52 IT departments across the city including the SFMTA, the airport, the school district and other disparate functions.
That, he said, was how he was able to convince every department to get onboard with using a common cybersecurity monitoring system when each has its own way of buying and using software, a manifestation of the city's complex bureaucracy. Many of those departments have their own IT budgets and teams, some purchasing and running their own computers, servers, applications and networks.
Makstman credits Mayor London Breed's office with making the cybersecurity shakeup possible. "It couldn't have happened without the support of the mayor and the Board of Supervisors to actually create the office of cyber security," he said.
"We need a unified body and they've created the Office of Cybersecurity in the city charter," one of only a few in the country for a big city, he said. No such chartered role exists for the CIO position, which is established in the city's administrative code instead.
In the new chief role, Makstman said he will have to work by influence and bargaining rather than by fiat.
"I think we can buy better. We can buy smarter. We can buy together," he said. That is less the work of a technical wizard than that of a politician, to convince 50-plus different departments doing things one way, his way, is the best way.
Q: How do you feel about using AI at the city level?
Makstman doesn't see the city diving in headfirst on AI. Although San Francisco is the global epicenter of the technology's development, he said he doesn't believe chatbots should be plugged into city services just yet.
"I'm really excited to bring this technology as an additional tool in our toolbox to delivering city services to San Franciscans, but also to staff," he said.
But a cautious approach is warranted.
"We've seen some of the municipalities kind of jump early into this and they had to pull back ... because the technology wasn't ready," Makstman said.
He said he has a personal ChatGPT subscription, and points to the city's AI guidelines last year encouraging city employees to experiment with the technology, if not deploy it into city systems, as sound.
Makstman said his staff is running tests with AI programs designed by Microsoft, Google, Amazon and others. He sees applications for AI such as visualizing and updating old computer code, or using chatbots to help with writing, as ways the technology could find its way into the workaday lives of city employees.
For the time being that is all in the experimentation phase.
Another reason to take it slowly, Makstman said, is that he worries AI chatbots can be susceptible to bias or inclined to a particular worldview incompatible with the city's commitment to serving all different types of people.
"Government services might not be the first one you want to try on your experimental technology," he said, adding that cutting edge technology "often fails exactly with the groups that we are charged with serving. With vulnerable communities, with people who don't speak English as their primary language," he said.
Q: How can young techies make the city work better?
"If you really want to contribute, this is not a hackathon," Makstman said. "Helping us solve our problems is not a weekend activity. It takes us technologists in government months and years to learn."
"People get frustrated. 'I have this brilliant app. Why isn't the city just adapting that? ' Well, that's the wrong conversation. I want people to come with an open heart, to understand what the real challenges are," he said. "Is the real challenge summarizing Muni documentation (with AI)? I don't know. Or is the real challenge to help folks to get the services that they need to get right at the time, in the place where they need to get them."
So what is Makstman's message to all of the tech talent pouring into San Francisco to work in the AI industry?
"My message to all of those bright folks is please come and work for government," he said. "We need your mind to really come to help us make a better future for San Francisco ."
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