Jobs › Chicago Trading Company
Senior Quantitative Trader - Delta One
Posted Sep 14, 2026 · We last checked this listing on Sep 20, 2026
Apply at Chicago Trading Company
Likely interview questions for this role
Written from this job description, not a generic list. Each one notes what the interviewer is really checking.
Behavioral
Walk me through a systematic strategy you built end to end, from the original idea to it running in production. What did it actually trade and how did you know it was working?
whether the candidate has genuinely owned the full research-to-production lifecycle versus just contributed pieces
Tell me about a time a backtest looked great but the strategy didn't hold up once it was live. What was different, and how did you catch it?
awareness of overfitting, transaction cost realism, and honesty about failure
Tell me about a time you disagreed with a researcher or engineer on your team about whether a strategy was ready to go live. How did that get resolved?
collaboration style and how they handle conflict with technical peers
Technical
How do you think about transaction costs and market impact when you're evaluating whether a signal in futures is actually tradable at size?
depth of practical execution knowledge versus purely academic signal research
Describe how you'd design a simulation environment for a new futures strategy from scratch. What pieces matter most to get right?
understanding of simulation fidelity, fill assumptions, and infrastructure design choices
What's your process for monitoring a live strategy day to day? What would make you pull it or resize it?
discipline around production risk management and decisiveness under uncertainty
Tell me about a cross-product or cross-asset relationship you've used in a signal. How did you validate that the relationship was real and not coincidence?
ability to reason about relative value and structural relationships across markets
How do you use Python, or whatever tools you rely on, when you're moving from a research notebook to something that can run reliably in production?
practical engineering maturity, not just research scripting ability
What's a market structure change in futures or delta-one products in the last few years that you think matters for how strategies should be built now?
currency of market knowledge and independent thinking rather than textbook answers
Situational
Say you find a signal that works well on E-mini S&P futures. How would you go about testing whether it generalizes to other delta-one products, or whether it's an artifact of that one market?
rigor in cross-asset validation and skepticism about spurious results
A strategy you built starts underperforming after a shift in market structure or liquidity. Walk me through how you'd diagnose whether to fix it, shelve it, or kill it.
judgment on strategy lifecycle decisions and resistance to sunk-cost thinking
You're given a junior person on the team who has a promising idea but a sloppy backtest. How do you mentor them through fixing it without just doing it for them?
mentorship approach and ability to raise the bar on team research quality
If two of your live strategies started fighting each other for the same risk or signal, how would you notice and what would you do about it?
portfolio-level thinking beyond single-strategy research
Practice this interview out loud.
Offer builds a real interview for this exact role at Chicago Trading Company from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.
Practice this out loudThe full job description
As published by Chicago Trading Company.
Apply at Chicago Trading Company
Related jobs
Quant Developer - Research Engineering
Posted Sep 17 · Verified Sep 20
Senior Engineer - Data Ingestion
Posted Sep 17 · Verified Sep 20
Recruiter – Technology (Contract)
Posted Sep 17 · Verified Sep 20
Equity Research Analyst
Posted Sep 11 · Verified Sep 20
Senior Compensation Analyst
Posted Sep 11 · Verified Sep 20
Business Manager - Systematic
Posted Sep 11 · Verified Sep 20