Headlands Technologies Interview Guide

Headlands is a proprietary quantitative trading firm. It is privately funded and takes no outside investors. The firm says it has designed and run quantitative trading strategies across many products and venues worldwide since 2010.

As of August 2026, Headlands is headquartered in Chicago and was founded in July 2009 by three former senior executives from Citadel's trading side: Matt Andresen, Jason Lehman and Neil Fitzpatrick. It sold its fixed-income affiliate, Headlands Tech Global Markets LLC, to Toronto-Dominion Bank in a deal completed in July 2021, and as of August 2026 it continues as a quantitative proprietary trading firm.

Headlands lists five offices, in Chicago, New York, Amsterdam, London and Singapore, and trades around the clock from them.

On 5 Nov 2026 the Headlands job board had 8 openings, and none had internship in its title. The two early-career postings were Quantitative Researcher (New Grad) and C++ Software Developer (New Grad).

To intern, apply to one of those two. Both forms have a required Desired Employment question with two answers: Full-time and Internship.

Quantitative Researcher (New Grad)

Open in Amsterdam, Chicago, London and New York. You research and build predictive signals and trading models to improve strategy PnL, and you own each idea from hypothesis to production, results included.

You need a degree in a highly technical field such as computer science, engineering, statistics, mathematics or physics, and a demonstrable interest in systematic trading. Internship experience is preferred.

The posting asks for strong statistics and machine learning, with practical experience on noisy real-world data. You also need solid software skills and practical experience in Java, C++ or Python. The firm wants low ego and someone who works well both with a team and alone.

C++ Software Developer (New Grad)

Open in Amsterdam and Chicago. You design and build the firm's trading software in C++.

The day-to-day work on the posting includes exchange connectivity, speeding up the live trading system with lock-free data structures and compiler intrinsics, measuring latency with microbenchmarks and profiling, and low-level network programming.

You need very strong C++, or experience in another statically typed imperative language. A computing degree is preferred, and extensive professional software experience can stand in for it. Trading experience is not required.

Training

In the firm's video on training, a staff member says new hires learn the whole system, because everything is open internally, and that getting someone up to speed can take a year or two.

Other roles

• FPGA Engineer: it asks for professional FPGA or ASIC design and verification experience, so it is not an entry-level role.
• Experienced C++, Java and quant researcher roles: the experienced researcher listing tells new grads to use the New Grad posting.
• Opportunistic Applications: a form for roles not on the website. It repeats the one-job-only rule and asks which role you want.

Headlands asks for one application because it reviews each candidate individually and considers your profile for every relevant opening.

The Quantitative Researcher (New Grad) form asks for:

• Your most recent transcripts (required).
• Your top three programming languages, each rated from 0 (no experience) to 3 (expert user).
• Other processes you are in, and any offers and their deadlines. Headlands says it will do its best to work around them.
• How interested you are in finance, from not interested to only considering finance. You do not have to be set on finance to apply.
• Your available start date.
• Optional written answers on why you applied and what your career goals are.
• Whether you need US visa sponsorship, now or later, if you pick a US location.

On the C++ form, the Education + GPA upload is optional and asks current students for their transcripts.

The privacy notice for applicants in the EEA, Switzerland and the UK lists aptitude tests alongside interviews, and says the firm uses applicant data to prevent assessment manipulation.

As of August 2024, an experienced engineer's online assessment question was one discussed on the LeetCode forum under the title "headlands oa".

If you have a disability or health condition, the same notice says the firm considers adjustments during a test or interview.

The Java Software Developer posting lists conducting interviews and candidate evaluations among a developer's duties, and a quant researcher in the firm's video says they do lots of interviews during the day.

In the firm's video on timing, a staff member says the team is very small, so Headlands moves people through the process and sends updates very quickly.

One engineer's interview, August 2024

As of August 2024, an experienced engineer who passed the online assessment had an hour-long Zoom call with an engineer, and got a rejection within 36 hours.

• As of August 2024, the first task was summing the first n natural numbers without the closed-form formula, in several ways (recursive, iterative, tail-recursive, and taking a vector or const vector as input), and the interviewer kept adding variants on what to change to make it run faster.
• As of August 2024, the second task was designing an optimised version of C++ unordered_map for mapping stock tickers to integers, with follow-ups on ways to implement it, cutting hash collisions and memory overhead, and optimising when the set of keys is known in advance or keys have a maximum length.

What Headlands looks for

A staff member says in the firm's video that you need to be smart, prolific and knowledgeable across maths, statistics, computer science and trading systems, and that the firm hires people who complement each other and come from different backgrounds.

In another video, a staff member says Headlands is a poor fit if you want to be told exactly what to do. After a few years, staff are expected to have independent ideas.