The White House hopes by incorporating the message of enrollment into videos it already makes, Funny or Die can help make the message go viral.
The administration is aided in its efforts by an array of independent groups.
The president's former campaign organization, now called Organizing for Action, is spending upwards of seven figures over the course of the summer for commercial time on cable stations to help educating people about the health care law.
The ads promote success stories about how the law impacts average Americans. By placing them on channels like Bravo, the group can target mothers who have outsized influence on their children's decision to purchase insurance.
Enroll America, a nonpartisan group focused solely on maximizing enrollment under the health care law, already has staff in 10 states where uninsured populations are highest.
With an advisory board that includes representatives from across the health care spectrum as well as consumer groups, community organizations, and charities, Enroll America will have more than 200 employees by October 1 working on a campaign geared toward connecting those seeking insurance with a plan available on their state marketplace.
Local effort in states
In states that chose to run their own exchanges, the effort is much more local.
Kentucky will be doing outreach for its exchanges at bourbon festivals in the fall, while California has partnered with Spanish-language television outlets to reach its state's uninsured youth, nearly half of whom are Hispanic.
A senior administration official said the effort is targeted and strategic.
"I think the enrollment strategy is both an effort to meet the needs of the uninsured but also the best political strategy as well, because once it's out there, once millions of people are enrolled, once states have programs up and running, it'll be very hard to put the genie back in the bottle," Altman said.
Some skeptics question how the administration will be able to convince young, healthy Americans -- often called "young invincibles" in health care conversations -- to spend money every month on insurance they may never use. But officials believe they can reach their goal of 2.7 million people if they can overcome two main obstacles.
"At the core of the obstacles is affordability and access and we've created a system that addresses that," a senior administration official said, pointing to government subsidies that help address affordability, and the redesigned Healthcare.gov that is intended to address ease of access.