Investigator

Insight Global; Chicago (IL); On-site; USD 85,000 - 115,000; Full time

Job summary

Insight Global is seeking a capable investigator for the Cboe Regulatory Division's Cross Market Surveillance team in Chicago. You will conduct real-time surveillance of orders and trading, engineer data-driven analyses with Python and advanced Excel, and document thorough investigative narratives.

You will triage alerts, enrich data, reconstruct timelines, and contribute to process improvements in data pipelines and alert thresholds to address regulatory concerns.

Qualifications

• Bachelor's degree in economics, business, accounting, finance, statistics, computer science or related field.
• 2+ years in securities/trading, preferably surveillance, compliance or risk.
• Proficiency in Python (pandas, numpy) and Jupyter notebooks.
• Advanced Excel with Power Query, pivots and complex formulas.
• SQL with performance, joins and window functions.
• Exposure to SIGMA, Snowflake or Big Data SQL environments a plus.
• Strong analytic and research skills; ability to handle detail-heavy problems.
• Excellent attention to detail and structured documentation.
• Clear written and verbal communication; able to distill market activity.
• Proficient in MS Office; diligent file management and audit trails.
• Self-driven, independent work ethic; able to interact with all levels.
• Extra Credit: SQL relational databases, VBA or Access for automation.
• Extra Credit: SMARTS Trade System Surveillance experience.

Responsibilities

• Conduct real-time and pattern-based surveillance of orders and trades.
• Analyze activity using Python (pandas) and advanced Excel; identify rule violations.
• Triage alerts, enrich data, reconstruct timelines and document findings.
• Summarize data into narratives and maintain organized case files.
• Support new surveillance processes, data pipelines and alert tuning.
• Prepare structured memos with evidence, rationale and conclusions.
• Develop understanding of exchanges rules and market microstructure.
• Collaborate with Options Investigations to improve signal quality.
• Participate in backtesting, data quality audits and automation projects.

Skills

Analytical thinking

Attention to detail

Strong communication

Self-motivated

Team collaboration

Education

Bachelor's degree in Economics, Business, Accounting, Finance, Statistics, Computer Science

Tools

Python (pandas)

NumPy

SQL

Excel (Power Query, pivot tables)

Jupyter notebooks

MS Office

SIGMA

Snowflake

Big Data SQL

SMARTS Trade System Surveillance

Access (VBA/automation)

Job description

Job Description

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”).

• 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).

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Skills and Requirements

• 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).
• 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.