Trump Team Eyes Politically Connected Startup to Overhaul $700 Billion Government Payments Program

Four days before Donald Trump’s inauguration, financial technology startup Ramp published a pitch for how to tackle wasteful government spending. In a 4,000-word blog post titled “The Efficiency Formula,” Ramp’s CEO and one of its investors echoed ideas similar to those promoted by Trump and his billionaire ally Elon Musk: Federal programs were overrun by fraud, and commonsense business techniques could provide a quick fix.

Ramp sells corporate credit cards and artificial intelligence software for businesses to analyze spending. And while the firm appears to have no existing federal contracts, the post implied the government should consider hiring it. Just as Ramp helped businesses manage their budgets, the company “could do the same for a variety of government agencies,” according to the blog and company social media posts.

It didn’t take long for Ramp to find a willing audience. Within Trump’s first three months in office, its executives scored at least four private meetings with the president’s appointees at the General Services Administration, which oversees major federal contracting. Some of the meetings were organized by the nation’s top procurement officer, Josh Gruenbaum, commissioner of the Federal Acquisition Service.

GSA is eying Ramp to get a piece of the government’s $700 billion internal expense card program, known as SmartPay. In recent weeks, Trump appointees at GSA have been moving quickly to tap Ramp for a charge card pilot program worth up to $25 million, sources told ProPublica, even as Musk’s Department of Government Efficiency highlights the multitudes of contracts it has canceled across federal agencies.

Founded six years ago, Ramp is backed by some of the most powerful figures in Silicon Valley. One is Peter Thiel, the billionaire venture capitalist who was one of Trump’s earliest supporters in the tech world and who spent millions aiding Vice President JD Vance’s Ohio Senate run. Thiel’s firm, Founders Fund, has invested in seven separate rounds of funding for Ramp, according to data from PitchBook. Last year, Thiel said there was “no one better positioned” to build products at the intersection of AI and finance.

To date, the company has raised about $2 billion in venture capital, according to startup tracking website Crunchbase, much of it from firms with ties to Trump and Musk. Ramp’s other major financial backers include Keith Rabois of Khosla Ventures; Thrive Capital, founded by Joshua Kushner, the brother of Trump’s son-in-law Jared Kushner; and 8VC, a firm run by Musk allies.

The special attention Gruenbaum paid to Ramp raised flags inside and outside the agency. “This goes against all the normal contracting safeguards that are set up to prevent contracts from being awarded based on who you know,” said Scott Amey, the general counsel with the bipartisan Project on Government Oversight. He said career civil servants should lead the process to pick the best choice for taxpayers.

A senior GSA official, who requested anonymity for fear of retribution, said the high level attention Ramp received was unusual, especially before a bid had been made public. “You don’t want to give this impression that leadership has already decided the winner somehow.”

GSA told ProPublica it “refutes any suggestion of unfair or preferential contracting practices,” with a spokesperson adding that the “credit card reform initiative has been well known to the public in an effort to address waste, fraud, and abuse.”

Ramp did not respond to requests for comment.

Rabois, one of Ramp’s earliest investors, is part of an influential group of tech titans known as the “PayPal Mafia.” Leaders of the early payments company include several influential players surrounding the Trump administration, including Musk and Thiel. Rabois and his husband, Jacob Helberg, hosted a fundraiser that pulled in upwards of $1 million for Trump’s 2024 campaign, according to media reports. Trump has nominated Helberg for a senior role at the State Department.

Rabois sits on Ramp’s board of directors. He has said he had no plans to join the Trump administration, instead telling CNBC: “I have ideas, I can spoon-feed them to the right people.” He told ProPublica his comments to CNBC were about big-picture policy ideas and that he had “no involvement in any government-related initiatives for the company.” Ramp “could be a great choice for any government that wants to improve its efficiencies,” Rabois added.

Helberg said he has no involvement “in anything related to Ramp whatsoever.”

Thrive Capital, Kushner’s firm, did not respond to a request for comment. A spokesperson for Thiel did not provide a comment. 8VC did not respond to a request for comment, nor did the White House or Musk; previously, Musk has said “I’ll recuse myself” if conflict-of-interest issues arise.

Ramp’s meetings with Gruenbaum — who comes from private equity firm KKR and has no prior government experience — came at an opportune moment. GSA will decide by year’s end whether to extend the SmartPay contract, and preparations are afoot for the next generation of the program. SmartPay has been worth hundreds of millions of dollars in fees for the financial institutions that currently operate it, U.S. Bank and Citibank.

Gruenbaum and acting GSA administrator Stephen Ehikian entered the agency with a strong belief that SmartPay and other government payment programs were rife with fraud or waste, causing huge losses, sources within GSA say — an idea echoed in Ramp’s January memo.

Yet both GOP and Democratic budget experts, as well as former GSA officials, describe that view as ill-informed. SmartPay, which provides Visa and Mastercard charge cards to government employees, enables the federal workforce to purchase office supplies and equipment, book travel and pay for gas.

The cards typically are used to fund travel and purchases up to $10,000.

“SmartPay is the lifeblood of the government,” said former GSA commissioner Sonny Hashmi, who oversaw the program. “It’s a well-run program that solves real world problems … with exceptional levels of oversight and fraud prevention already baked in.”

Jessica Riedl, a GOP budget expert at the conservative Manhattan Institute think tank, said the notion that there was significant fraud in the charge card technology was far-fetched. She had criticized waste in government credit card programs before the latest SmartPay system was implemented in 2018.

“This was a huge problem about 20-25 years ago,” she said. “In the past 15 years, there have been new controls put into government credit card purchases.”

A 2017 audit of the program by the Government Accountability Office concluded there was “little evidence of potential fraud” in SmartPay small purchases, though it found documentation errors. More recent government audits found some instances where officials did not always use anti-fraud tools.

GSA’s new leaders are convinced SmartPay is entirely broken, a view they shared in private meetings, sources said. In February, they put a temporary $1 limit on government cards and severely restricted the number of cardholders, choking off funds to workers in the field.

Chaos ensued across the government, news organizations reported: Staff at the National Institutes of Health were reportedly unable to purchase materials for experiments, Federal Aviation Administration workers worried they would be unable to pay for travel to test systems in the field, and National Park Service employees could not travel to oversee road maintenance projects.

At the time, GSA released a statement saying the limitations were “risk mitigation best practice” and internally began moving to revamp SmartPay.

$25 Million Opportunity

Ramp’s first bite of the SmartPay business could come through a pilot program worth up to $25 million that GSA announced several weeks after agency leadership began meeting with the company.

At the tail end of the Biden administration, GSA had sent out a request for information, or RFI, seeking industry input about how to improve the next iteration of SmartPay. But some industry players who submitted responses said they did not hear back from the government. Instead, GSA started meeting with Ramp.

GSA put out a new RFI for the pilot program on March 20, 2025, leaving it open for less than seven business days.

John Weiler, co-founder of the nonprofit research group the IT Acquisition Advisory Council, said such a short window appeared unusual. “A week is nothing, it gives the impression they had already picked the winner,” said Weiler, who has worked with Republican Sen. Chuck Grassley to investigate IT contracting issues.

Ramp is the clear-cut “favorite,” to secure this work, one source inside GSA and another former official told ProPublica. The winner has not yet been announced.

Procurement experts told ProPublica that consulting with industry leaders before a major overhaul is good practice — but that the fact-finding process must be evenhanded and led by professional contracting officers.

The GSA spokesperson said that “any and all communications with potential vendors, of which there were multiple, has been a part of market research in order to provide the best solution for American taxpayers.” The agency declined to answer questions about whether Ramp had already been chosen internally for SmartPay work.

The pilot program is unique because it uses a special GSA purchasing authority known as commercial solutions opening. This process has been used by the Pentagon to help speed up the acquisition of products for fighters in armed conflict zones. The designation means the chosen contractor can be selected faster and without the same level of controls.

It’s not clear how Ramp originally secured private meetings with GSA leaders. Nor is it clear if Ramp will ultimately take over the entire SmartPay contract from Citibank and U.S. Bank. Spokespeople for U.S. Bank and Citibank declined to comment.

It is clear that Ramp has never had a client like the federal government. The only public-sector partner listed on its webpage is a charter school network in Nashville, Tennessee.

Still, even before the RFI was publicly announced, Ramp had begun reaching out to contacts in the payment industry asking about the special bank identification numbers required to process government payments, said an industry source. Such steps, two former GSA officials said, were another sign that Ramp was preparing to work on the program.

Ramp’s meetings with GSA come as the agency is poised to take on a more significant role in spending decisions across government. The same day the SmartPay pilot was announced, Trump issued an executive order that seeks to centralize much of government procurement inside of GSA. The DOGE initiative has been effectively headquartered out of the agency — staffers have installed beds and dressers for overnight stays in the building, and Musk’s right-hand man Steve Davis is a key adviser to the agency’s leadership.

The SmartPay contract negotiation has so far flown under the radar. But changes to the credit card program could further transform daily life for federal employees and fundamentally change how agencies operate. It also represents a giant business opportunity.

“There’s a lot of money to be made by a new company coming in here,” said Hashmi, the former GSA official. “But you have to ask: What is the problem that’s being solved?”