Headlands was founded in July 2009 by three former senior executives from the trading side of Citadel Group.[2] Matt Andresen was a former co-chief executive at Citadel Securities. At the same time, Jason Lehman was head of Citadel's global options business, and Neil Fitzpatrick was chief operating officer of Citadel Execution Services. The partners secured outside funding to start the firm and set up its quantitative trading operation to trade equities, options, and futures. The trading would be computer-driven, and the firm would not run outside money. At the start, the firm had ten employees.[3][4][5][6]
In 2013, Headlands Tech Global Markets LLC was established to trade Fixed income securities. In 2014, it started trading municipal bonds and focused mostly on lots of $100,000 or less. In 2019, it was reported to execute more than 1,000 trades daily and had an inventory of $400 million. Its technology could generate prices on more than 700,000 bonds.[6][7]
In March 2021, Toronto-Dominion Bank agreed to buy Headlands Tech Global Markets LLC from Headlands to improve its automated fixed-income trading platform.[7][8] The deal was completed in July 2021.[9]
In 2022, Headlands had tripled the size of its office in Chicago by leasing floors in other office buildings.[10]
In January 2025, United States prosecutors alleged that the former trader Richard Ho had stolen intellectual property trade secrets from Headlands. Headlands alleged that Ho had colluded with Tower Research Capital.[2]
