Alex Brownstein explains why he sees Olmstead’s turnover of four CFOs in 14 months as a strategy problem and identifies the underlying issues.
On July 9, Nate Olmstead becomes the fourth person to run finance at The Trade Desk in 14 months. The company calls the churn a changing of the guard. Coming from where I sit, it reads as a strategy question, not an HR one.
Start with the roster, because it’s public and it’s long. Laura Schenkein, CFO since 2023 and a nearly 12-year insider, out in August 2025. Alex Kayyal, a venture investor who joined the board and then stepped into the operator seat, gone after about five months. Tahnil Davis, the chief accounting officer, held it on an interim basis. Now Olmstead. In the same stretch the company also lost its CMO (Ian Colley, now at DeepIntent), its chief revenue officer (Anders Mortensen, after seven months), its chief strategy officer (Samantha Jacobson, who left for OpenAI and kept her Trade Desk board seat), its head of communications, and the SVP who ran Ventura, its connected-TV business (Matthew Henick, now CEO of Meow Wolf). The stock fell about 7% the day the first wave of departures broke.
Five departures made the headlines. Four CFOs in one seat is the number I’d stare at.
Start with the CFO seat
The three CFO profiles don’t line up. Schenkein built the finance function from the inside through the growth years. Kayyal came out of venture capital, an investor asked to operate a public company’s P&L. Olmstead arrives from Penguin Solutions, an AI-infrastructure company where he was CFO, after running finance at Logitech and 16 years across HP and HPE.
Olmstead is the one who fits what the company actually is now. It took four tries to land a mature-P&L infrastructure CFO because it took the company that long to accept it had become a mature-P&L infrastructure business, and not the hypergrowth story it hired the first three people to steward.
The deal that built the company
The Trade Desk was built on a specific promise to the agencies. In 2016, before the IPO, Jeff Green told AdExchanger the plan was to “go to the agencies with the idea that we were going to power them, not compete with them.” The whole model was to be the neutral buying platform an agency could stand on without worrying it would turn around and take the client directly. It worked well enough to carry the company into the S&P 500 in 2025.
Read the article, The Trade Desk Has Hired Four CFOs in 14 Months. The C-Suite Emptied Around Them. The Product Outgrew the Sales Team, and Nobody Wants to Say It, on LinkedIn.