Headlands Technologies

When three senior leaders walk out of Citadel together, the new firm starts well-capitalized. Headlands Technologies came together in 2009 from exactly that: Matthew Andresen, who had co-run Citadel Securities, options chief Jason Lehman, and execution COO Neil Fitzpatrick, building a privately funded quantitative market maker that takes no outside investors and trades its own book around the clock.

Its most distinctive line of business was the one it sold. In 2013 Headlands spun up a fixed-income arm that automated pricing across hundreds of thousands of municipal and corporate bonds, quoting a corner of the market most people still traded by phone. TD Bank acquired that business in 2021, folding it into TD Securities. The parent kept its equities, options, and futures trading, run from Chicago across offices spanning Amsterdam to Singapore time.