Jobs › Cboe Global Markets

Investigator

Cboe Global Markets · Chicago, IL · $79,475–$102,850 a year · Full time

Posted Sep 25, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about an investigation or analysis you did where the evidence was unclear. How did you reach a conclusion?

What they are checking: Whether they handle ambiguity carefully and base conclusions on evidence.

Tell me about a time you learned a complex topic quickly to do your job.

What they are checking: Whether they can master products and rules fast in a technical regulatory role.

What would you do

An alert shows a firm trading VIX futures heavily just before options settlement. How would you approach it?

What they are checking: Whether they can reason about settlement-related manipulation and gather the right data.

During real-time surveillance, you see something suspicious happening right now. What do you do?

What they are checking: Whether they know when and how to escalate immediately in live markets.

How do you stay objective when reviewing a firm that's important to the exchange's business?

What they are checking: Whether they keep regulatory independence regardless of who the firm is.

About the work

How would you look for manipulation that spans Cboe Options and CFE futures at the same time?

What they are checking: Whether they understand cross-market schemes where activity in one market benefits a position in another.

What's the difference between real-time surveillance and pattern-based surveillance, and what does each catch?

What they are checking: Whether they understand both kinds of review this role performs.

What tools or queries would you use to reconstruct a firm's activity across two markets?

What they are checking: Whether they are technically proficient with data, which the posting emphasizes.

How do you document a case so another investigator or a legal team can follow it?

What they are checking: Whether they write clear records that support possible enforcement action.

What do you understand about the self-regulatory duties of an exchange?

What they are checking: Whether they know why the Regulatory Division exists and who oversees it.

How would you tell a legitimate hedging strategy apart from manipulation across markets?

What they are checking: Whether they consider intent and economic rationale before drawing conclusions.

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The full job description

As published by Cboe Global Markets.

Job Description: Building trusted markets — powered by our people At Cboe Global Markets, we inspire our people to solve complex challenges together because what we do matters. We provide the financial infrastructure that powers the global economy. As a leading provider of market infrastructure and tradable products, Cboe delivers cutting-edge trading, clearing and investment solutions to market participants around the world. We’re building meaningful ways to support professional and personal development while strengthening the trust we’ve earned as a global market leader. Our teams are empowered to share ideas, actively pursue them and bring on a challenge. As champions of internal mobility and access to opportunity, we encourage our people to “go for it” and equip our managers with the training to coach their teams to the next level. We strive to provide employees a safe space to network, share ideas and create opportunities. Role: Cross Market Investigator, Regulation The Cboe Regulatory Division (the “Division”) is actively seeking a highly motivated, technically proficient individual to join our Cross Market Surveillance team. The investigator will conduct real-time and pattern-based surveillance to assist in determinations of potential rule violations of Cboe Options and CFE Futures Exchanges (collectively, the “Exchanges”) Rules, along with other applicable rules and regulations governing Exchange Members and Trading Permit Holders (“TPH”). Work Location: Hybrid role with required in-office presence Monday through Thursday each week. Office location: Chicago, IL. Duties and Responsibilities: • Conduct surveillance and analysis of order entry and trading activity on the Exchanges to detect potential violations of Cboe and CFE rules and policies, with heavy use of Python (pandas) and advanced Excel (Power Query, pivot tables, complex formulas). • Leveraged AI-assisted analytics and Python (pandas, NumPy) to identify patterns in cross-market trading activity, improving surveillance signal quality, reducing manual review time, and accelerating end-to-end investigations. • Investigate alerts end‑to‑end: triage, validate, enrich with contextual data, reconstruct timelines, and document detailed findings suitable for review and potential escalation. • Analyze and compile data into meaningful summaries and investigative narratives; maintain organized case files, update working datasets promptly, and make findings accessible to the team. • Contribute to new surveillance processes and operational methodologies, including data pipelines, query logic, and tuning of alert thresholds to address evolving regulatory concerns. • Conduct rule‑based investigations to ensure compliance with Exchanges rules; prepare structured memos that clearly lay out evidence, rationale, and conclusions. • Develop and maintain deep understanding of the Exchanges’ regulatory environment, relevant rules and regulations, market microstructure, technologies and systems, and investigative/examination techniques. • Collaborate with cross‑functional partners, particularly the Options Investigations team, to improve signal quality, share insights, and deliver effective, efficient surveillance outcomes. • Participate in special projects (e.g., backtesting surveillance logic, data quality audits, automation of repetitive workflows, and retrospective reviews). Skills and Experience: • 2+ years of experience in the securities/trading industry (derivatives experience preferred), ideally in surveillance, compliance, or risk. • Python (pandas, numpy; comfort with Jupyter notebooks and reproducible analysis). • Excel (advanced): Power Query, pivot tables, nested formulas, data cleansing, reconciliation. • SQL: ability to write performant queries, joins, window functions, and QA data outputs. • Preferred data stack exposure: SIGMA, Snowflake, and Big Data SQL environments for large‑scale investigative analysis. • Exceptional analytical and research skills, with the ability to apply both quantitative and qualitative analysis to ambiguous, detail‑heavy problems. • Strong attention to detail and organization; comfortable with tedious, repetitive alert work and thorough documentation that stands up to scrutiny. • Clear and effective communication skills (written and verbal)—capable of distilling complex market activity into concise, structured findings. • Highly proficient in MS Office suite; experience with versioning of analyses and artifacts (e.g., disciplined file management, clear naming, audit trails). • Self‑driven and dependable, able to work effectively and independently with all levels of management and staff; motivated by mission‑critical work that improves market integrity. • Extra Credit: Experience with relational databases SQL, VBA, or Access for workflow automation. • Extra Credit: Experience with SMARTS Trade System Surveillance software. Education: Bachelor’s degree required; economics, business, accounting, finance, statistics, computer science, or related fields (preferred). Advanced degree preferred (e.g., MS in Data Science/Statistics/Economics/Finance, MBA). Benefits and Perks of working for Cboe Global Markets We value the total wellbeing of our people – including health, financial, personal and social wellness. We believe standard benefits like health insurance and fair pay are a given at any organization. Still, you should know we offer: • Fair and competitive salary and incentive compensation packages with an upside for overachievement • Generous paid time off, including vacation, personal days, sick days and annual community service days • Flexible, hybrid work environment • Health, dental and vision benefits, including access to telemedicine and mental health services • 2:1 401(k) match, up to 8% match immediately upon hire • Discounted Employee Stock Purchase Plan • Tax Savings Accounts for health, dependent and transportation • Employee referral bonus program • Volunteer opportunities to help you give back to your communities Some of our associates’ favorite benefits and perks include: • Complimentary lunch, snacks and coffee in any Cboe office • Paid Tuition assistance and education opportunities • Generous charitable giving company match • Paid parental leave and fertility benefits • On-site gyms and discounts to other fitness centers • Paid Time Off More About Cboe Global Markets We’re reimagining the future of the workplace by focusing on what matters most, our people. Our journey is an inclusive one. We’re investing deeply in leadership programs and career development initiatives that ensure everyone has an equal chance to succeed. We work with purpose, solving problems with ingenuity, collaboration, and a lot of passion. We’re an engaged and excited team connecting markets across borders and embracing growth in all its forms to achieve incredible outcomes. Learn more about life at Cboe on our website and LinkedIn. Equal Employment Opportunity We're proud to be an equal opportunity employer do not discriminate against any employee or applicant for employment based on any legally protected characteristic, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, or veteran status. We are committed to fostering a workplace where all individuals are valued and respected. This position is not eligible for visa sponsorship. Candidates must be legally authorized to work in the United States without the need for employer sponsorship now or in the future. Salary Ranges (applicable for US locations only) At Cboe, we are committed to providing a competitive, transparent, and market‑informed total rewards program. The anticipated base salary range for this role is $79,475-$102,850, with actual compensation determined by job‑related factors such as skills, relevant experience, education, internal alignment, and location. This role may also be eligible for annual incentive compensation and, where applicable, participation in Cboe's long-term equity programs. Additional information about Cboe's total rewards program, including benefits and other compensation components, can be found here: Total Rewards at CBOE . ​ Any communication from Cboe regarding this position will only come from a Cboe recruiter who has a @cboe.com email or via LinkedIn Recruiter. Cboe does not use any other third party communication tools for recruiting purposes.

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