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Michael Dickerson: The invisible man behind Obamacare's tech surge

Mikey Dickerson
“If anybody deserves praise, it’s Mikey,” one source, close to the tech campaign to fix healthcare.gov, said of Dickerson. “Nobody is taking victory laps right now, but I’d single him out — he’s produced actual results.” (Photo by James Duncan Davidson)

The person most responsible for repairing the botched healthcare.gov website has no official title.

If Jeffrey Zients, President Obama's “Mr. Fix-It,” is the public face of the Obamacare cleanup effort, Michael Dickerson, a site-reliability engineer on leave from Google, is the invisible man overseeing hundreds of urgent repairs.

Technically, Dickerson is a subcontractor for Quality Software Services Inc., the company tasked by the Obama administration with fixing the glitch-ridden online marketplaces.

He was recruited because of his private-sector chops, which the administration thought would increase the odds of salvaging the most comprehensive overhaul to health care since Medicare.

His public persona, though, hardly draws attention to the enormity of his undertaking.

Dickerson's LinkedIn page reads simply, “No Fancy Title, Thanks at QSSI.” Listed among his self-described skills are “herding cats” and “breathing.”

After nearly four years as a systems administrator at California’s Pomona College — where he earned a bachelor’s degree in mathematics — Dickerson took a job at Google in early 2006 despite harboring some doubts. Like many in his field, the tech wizard catalogued his thoughts online.

“In the half-full glass,” said the then-26-year-old, “if things go well at Google, and the bonuses and stock options turn out to be worth something, then I should have, well, enough money for gum.”

In breaking down the pros and cons of his move to Google, Dickerson lamented the loss of a less ambitious slate of daily activities: “Sleep until 11, go to lunch, take nap on toilet, play Quake.”

Fast forward eight years and Dickerson is getting up early and trying to save healthcare.gov.

The administration in late October brought in private-sector experts to address an avalanche of technical snags that undercut Obama’s signature domestic achievement. In addition to Dickerson, Obama surrogates touted Greg Gershman, a former Presidential Innovation Fellow, to spearhead the so-called “tech surge.”

Those closely involved with the war-room efforts in Columbia, Md., said Dickerson helped untangle the website’s pretzel-like organizational structure and brought order to a project desperately in need of a reboot.

“If anybody deserves praise, it’s Mikey,” one source, close to the tech campaign to fix healthcare.gov, said of Dickerson. “Nobody is taking victory laps right now, but I’d single him out — he’s produced actual results.”

According to administration officials, more people enrolled in Obamacare insurance plans during the first two days of the website’s December relaunch than over the entire month of October. Those figures represent both progress and the pitiful state of the Obamacare website after open enrollment began on Oct. 1.

The tech team isn’t in the clear yet, however. Insurers have voiced concerns about difficulties delivering enrollment information on consumers, back-end hitches that the administration has been reluctant to discuss.

The Centers for Medicare and Medicaid Services did not make Dickerson available for an interview or respond to requests for information about his role in repairing the problem-plagued, federal website. Dickerson also did not respond to queries from the Washington Examiner.

Making Dickerson’s role all the more important, said one tech-team insider, is that just a “handful” of people are responsible for fixing the most chronic problems with healthcare.gov. Despite all the administration’s hyped-up rhetoric about a legion of tech experts tackling Obama’s self-inflicted wound, the Maryland war room consists of a small team of professionals.

John Engates, the chief technology officer of Rackspace Hosting, recently toured the Maryland war room at a time when the website wasn't accepting new users. Engates, who previously called healthcare.gov, “one of the most spectacular public failures of any website ever,” watched Dickerson in action.

"It was the way it should have been all along; I was impressed they were actually on the right track," Engates said. "They had accountability… Mikey had the authority to make people do the things they needed to do."

Engates said Dickerson would succeed because at Google he encountered problems on an hourly basis that others rarely see.

Zients, a former management consultant who will become Obama’s top economic adviser in January, recognized the need for an outside company to take charge. However, Zients is no technology expert — a fact that highlights the pivotal role played by Dickerson and his small band of troubleshooters.

Dickerson was a natural choice for the Obama administration, analysts said. He has a history with the president, having worked on the analytics team for Obama’s re-election campaign. In his online resume, Dickerson said he helped design the campaign’s election-day modeling, wrote a tool ranking the importance of get-out-the-vote contacts and created the algorithm for matching political ads to voter behavior.

Both of Obama’s presidential bids were bolstered by an unprecedented focus on data crunching, a technical prowess that made the rollout of healthcare.gov all the more glaring, some Democrats complained. As such, they wanted Dickerson — and other campaign alumni — to save the website.

“I'd just take the whole campaign tech team,” said a veteran Democratic strategist with close ties to the White House. “Those are people you know will get the job done.”

“Things are looking better for the website right now, but ask me again in a few weeks,” the strategist cautioned. “The champagne is still on ice.”