A flow chart of the hierarchy at Health and Human Services, as it stands now. Secretary Sylvia Burwell wants to add in a new position - CEO of HealthCare.gov - with a straight line reporting up to her.
A flow chart of the hierarchy at Health and Human Services, as it stands now. Secretary Sylvia Burwell wants to add in a new position - CEO of HealthCare.gov - with a straight line reporting up to her. - 

File this under one of the toughest jobs in America.

The federal Department of Health and Human Services (HHS) is beating the bushes for a CEO of HealthCare.gov, the site that became a punch line on late night TV last fall.

The Obama Administration wants to make sure the funny guys get material from somewhere else. New HHS Secretary Sylvia Burwell hopes appointing a CEO to oversee the operation will make the jokes go away.

The first thing the CEO must understand? That HealthCare.gov is an online store that exists to sell a product, and that product isn’t exactly a "hot ticket."

Health insurance is “a grudge buy,” says Jon Kingsdale, the first executive director of the Massachusetts exchange, known as the Massachusetts Health Connector.

“Nobody likes to go down to their corner broker’s office on a Saturday morning, like they do a car dealer, and smell the print on the new 150 page explanation of benefits, [or] see how fast they can get it from $0 to $60,000 in claims.”

Of course the federal government’s “glitchy” website only made it harder for consumers to kick the tires on those insurance policies.

As last year’s fiasco proved, running a public exchange – which covers two-thirds of the states - is uncharted territory for Washington.

Kingsdale says it’s a more entrepreneurial enterprise than most anything else the government does.

“I used to shock my very liberal, left-leaning board of directors by reminding them if you want to talk about enrollment and getting people covered, you are basically talking about marketing and sales,” he says.

By announcing plans to hire a CEO, many think HHS Secretary Sylvia Burwell understands this operation requires a business approach, with business savvy.

The new executive will work with state exchanges, consumers and insures.

Former White House advisor Kavita Patel says if HHS is going to call this person a CEO, Burwell must give the person the power of a CEO.

"As we saw with the rollout, people didn’t have the resources or authority to make the decisions they needed, and in the end, we suffered for it,” she says.

While Patel likes the idea of these management changes, it’s easy to see how the CEO could get buried in the federal government maze. 

He or she will run what’s called the Center for Consumer Information and Insurance Oversight - a bureau within the Centers for Medicare and Medicaid, a division of HHS.

“Imagine taking a new start-up organization and putting it inside IBM. Something with 20,000 divisions, 200 senior vice presidents,” says Patel.

In a statement last month, Burwell said the CEO will have a “dotted line” straight to her.

In other words, this new management structure is supposed to help Burwell stay in the loop – poised to move if calamity strikes.

Leadership - though - is just one challenge facing the feds as we approach HealthCare.gov 2.0.

“Let’s say you are Aetna, Cigna, United, Blue Cross - they are in the middle of doing incredibly complicated bids right now for 2015, with lots and lots of open questions,” says Tom Scully, former CMS Administrator under George W. Bush.

Scully says the CEO must understand what it’s like to develop new insurance policies, and how to get consumers to buy them. Someone, he says, who knows the industry inside and out: “You are probably going to know when someone is coming crying screaming at you, or whether they are crying wolf, or have a real problem.”

Kingsdale, the former head of the Massachusetts exchange says here’s the thing: HealthCare.gov is here to stay.

He says that means the federal government must do things like "enhance the consumer experience", and hold insurers' hands - or keep their feet to the fire.

“As the exchange matures from the start-up to this more commercial, entrepreneurial phase, this is a chance for the Obama Administration to show that the government can learn from the private sector,” he says.

Kingsdale says the more HHS accepts that it’s running a unique online store, serving as middleman to frequently overwhelmed shoppers and frequently frustrated insurers, the more people get insurance.

Which, he says, is the whole point. 

Follow Dan Gorenstein at @dmgorenstein