From the Cover of ‘Time’ Back to Campus, Mikey Dickerson ’01 Pilots ‘Return to Pomona’

Mickey Dickerson stands in front of classroom of students.

Before he landed on the cover of Time magazine, Mikey Dickerson ’01 was a mathematics major at Pomona College. That’s a bit surprising, since he earned his professional reputation as part of the crack “trauma team” of computer scientists that in 2013 rescued Obamacare’s massively flawed website. But in 1997, when he came to the College from Cromwell, Connecticut, computer science (CS) was not yet a major at Pomona. His formal CS education included just three courses spread between Pomona and Harvey Mudd.

Looking back, “I might have picked math anyway,” Dickerson says. In a math major, he explains, there is still “a very large amount of overlap with what you would get in a more theoretical CS degree.” And besides, he’d been teaching himself how to program since grade school.

Fast forward a dozen years. The Affordable Care Act—almost universally known as Obamacare—had become the law of the land, passing on the thinnest of margins in Congress and surviving multiple legal challenges in the courts. Its cornerstone, an online exchange where Americans could buy individual health insurance, depended on a website billions of dollars in the making that turned out not to work. At least, it didn’t perform at the scale necessary to meet the overwhelming demand. The result was agonizingly long wait times for users trying to log in—if the site didn’t crash in the meantime.

Joining the “rescue team”

Enter Dickerson, who was working in the new field of site reliability engineering (SRE) at Google, where he’d been recruited after a short stint as part of the academic staff at Pomona College. If he could manage teams that kept Google up and running 24/7/365 while users did nearly 100,000 queries per second, surely, thought Obama administration leaders, he could help fix a broken government website. Or at least figure out what was wrong. He joined the ad hoc rescue team “for what I thought was going to be two or three days,” he recalls. It turned out to be four or five months with little sleep, no vacation, and, in the end, a payoff in the satisfaction of helping bring health coverage to millions of Americans who might otherwise have remained uninsured.

“People will dispute the details of whether [Obamacare] is good policy or not,” Dickerson remarks. “But if you do the math, there’s a reasonable guess that there are a few hundred thousand people who would have died sooner” because without insurance “they didn’t have access to treatment. That’s not an outcome that you think of when you’re deciding to major in computer science.”

If Dickerson could be a key player in fixing the Obamacare exchange website, why not scale up and ask him to do the same for other antiquated information technology systems in the federal government? Thus, in August 2014, Dickerson found himself in an office near the White House as a special assistant to the President and administrator of the new U.S. Digital Service. He held the appointed position until the end of the Obama administration. In the newly created role he advised the President and leaders in the national security, economics and domestic policy councils and testified to Congress. Among the unexpected perks—an invitation to a state dinner for Indian Prime Minister Narendra Modi. Dickerson ditched his trademark comfortable jeans and rumpled shirts for black tie at the star-studded affair.

Return to Pomona

This spring semester, in an elective computer science class and lab titled “Managing Complex Systems,” Dickerson is sharing with students what he has learned in an eventful two decades since graduating from Pomona. He is helping the dean of the College pilot a new program, “Return to Pomona,” through which alumni in a variety of fields will teach, lecture and mentor on campus. In addition to the course, Dickerson will lecture at Alumni Weekend and in a faculty speaker series, as well as provide career advice for students.

“The Return to Pomona program is a part of the College’s mission and vision,” says Melanie Wu, vice president for academic affairs and dean of the College, who is herself a professor of computer science. Alumni like Dickerson “can provide career advice for students by bringing their work experience to campus, teaching a class and engaging them to think not only about today’s knowledge in the classroom but how to apply that in the future.”

Alumni engagement in the program may take a variety of forms, says Wu. Some alumni might teach full time for a year or more, while others might teach a single course, give a talk or interact with students for a week. Associate Dean April Mayes is coordinating the new program.

Providing “an accelerator”

In his class, Dickerson’s students get hands-on experience with industry tools and practices so that, as he sees it, “they’ll have an accelerator—an easier first two years in their careers.” His current work as a consultant to large, complex companies and organizations gives him a birds-eye view of the types of issues they are likely to face. “I’ve done a lot of hiring of new computer science undergraduates,” he says. The idea of the class is to give students “an experience that fills in a bunch of things that I know college graduates don’t usually know.”

Sage Santomenna ’26, a physics major, says “you can read all the instruction manuals and all the career-building guides you want. But when you get to the places where you actually have to deal with these complex systems, [Dickerson] tells you what it’s actually like.” Justin Long ’24, a computer science major, agrees. “In a field like this, where it seems like the protocols and the ways to do things are always changing, it’s really important to have someone who has seen it before and who knows how to adapt.”

Students arrive early for Dickerson’s Monday and Wednesday afternoon class. The room is full, and a number of the students are still engaging with the day’s topic after the formal class ends. In the evening lab, their project is to assemble and run a live Amazon Web Services site, setting up web servers and databases and keeping it fully functional. “It’s going to be continuously monitored for uptime,” Dickerson says. “So part of their grade is going to be ‘Does it stay available 24 hours a day, seven days a week?’”

Dickerson sees his job as supporting the students as they turn theory into practice. After tackling the issues he’s faced in his career so far, “They’re not likely to invent a problem that I can’t figure out,” he says.

Preparing students for jobs yet to come

When Dickerson was recruited from Pomona to do site reliability engineering at Google 17 years ago, “it turned out to be kind of the first cohort of SRE” at the company, he recalls. “There wasn’t any possibility of there being a class that would prepare me for that job because that job didn’t exist.”

His experience informs his Pomona teaching, just as the Return to Pomona program envisions. “The class I’m doing now I hope gives the students an idea that there are these types of software engineer-adjacent jobs out there that might be the thing they want to do,” Dickerson says. “They’re certainly going to have a head start over people elsewhere who’ve done four-year CS degrees that didn’t have this kind of practical exercise built into it.”

George Johnson ’24, who is majoring in computer science and economics, says, “This class embodies for me all the best parts of liberal arts.” He finds that it includes not only computer science but economics and philosophy as well. “It has already taught me to think more flexibly and be more capable of understanding broader institutions and rule sets that we just take for granted,” he says. “This is probably my favorite class that I’ve taken so far.”