Investigator

About the role

Cboe Regulatory Division is seeking a highly motivated, technically proficient individual to join the 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 Rules, along with other applicable rules and regulations governing Exchange Members and Trading Permit Holders.

Work location

Hybrid role with required in-office presence on designated days each week (specific days communicated during interview process). Office location: Chicago, IL.

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)
• Leverage 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)

Qualifications

• 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)

Skills

• 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

Benefits

• 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
• 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

Pay

Anticipated base salary range: $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.