The Priorities USA Action ad, titled "Romney's World View," features a 1985 photo of Romney standing with colleagues at Bain Capital with cash in their hands, mouths and pockets, while a narrator blasts the former CEO for his work at the company and current tax proposals. Romney himself is in the center with bills in his hands.
The 30-second spot will appear on television and online in Florida, Iowa, Ohio and Virginia, four swing states in the upcoming presidential election.
Romney's wealth has been an issue for the GOP presidential hopeful on the campaign trail, as opponents aim to paint him as out of touch with average Americans.
He defended the photo in an interview with Fox News back in December, saying it was taken on the heels of raising money for the private equity firm's first fund.
"We posed, just celebrating the fact that we raised a lot of money and then we hoped to be able to return it with a good return and in the interim we of course would have to be successful, build enterprises. That first fund got invested in a number of businesses that turned out to create a lot of jobs and yielded a very positive return for the people who entrusted us with their funds," Romney said.
A prescient Romney added, "I know that will be used. I know that … the president's going to go after me. I'll go after him."
Tax reform has been a major campaign issue in recent weeks, with Obama pushing his "Buffett Rule" proposal and Tax Day approaching Tuesday.
"On Tax Day, Americans should know that Governor Romney already pays a lower tax rate than middle class families but still believes the wealthiest one percent are entitled to massive new tax breaks paid for by cutting Medicare for seniors and education for the middle class," said Bill Burton, senior strategist for Priorities USA Action in a statement Monday.
Romney's tax plan, released in February, calls for a 20 percent across-the-board cut to individual tax rates, would reduce the corporate tax rate and put an end to the capital gains tax for most taxpayers.
He called for a "simpler, flatter and fairer" tax system in a speech after releasing his proposal.
"We've got to have more jobs, less debt and smaller government," he said in the speech. "They go together."
Lawmakers returned to Washington Monday and are poised to begin battling over their competing tax proposals.
Senate Democrats are planning a Monday vote on the so-called Buffett Rule, which sets a minimum tax rate for individuals with annual incomes a million dollars or more and phases that rate in for incomes between $1 million and $2 million. In the House, Republicans on Thursday are bringing to the floor a 20 percent tax cut for small businesses that Majority Leader Eric Cantor (R-Va.) has championed.
Neither proposal is expected to make it into law, despite Obama's repeated use of his bully pulpit to pressure Congress on the Buffett Rule.