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.

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.