Full-Time

Senior Surveillance Analyst

Tastylive

Tastylive

51-200 employees

Real-time trading insights and education platform

Compensation Overview

$101k - $120k/yr

+ Discretionary Performance Bonus + Stock Purchase Options

Chicago, IL, USA

In Person

On-site role located in Chicago, IL; work from the West Loop office.

Bachelor's, Master's, PhD

Category
Legal & Compliance (1)
Required Skills
SQL
Blockchain
AWS
Data Analysis

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Requirements
  • 2–5+ years of trade surveillance and/or AML transaction-monitoring experience at a broker-dealer, FCM, exchange, or regulator; experience building or materially enhancing a surveillance program is a strong plus (versus solely operating an out-of-the-box tool).
  • Active licenses: Series 7, Series 63 (or 66), and Series 3 (National Commodity Futures) required; Series 24 preferred.
  • Sound working knowledge of relevant rulebooks and regulations, including FINRA Rules 3110/3310, SEC Rule 15c3-5, NFA Compliance Rules 2-4 and 2-9, CFTC Rules 180.1/180.2, CEA Section 4c(a), the Bank Secrecy Act (BSA), the USA PATRIOT Act, and AML/KYC requirements for broker-dealers and NFA introducing brokers, plus awareness of applicable crypto/digital asset regulatory frameworks.
  • Demonstrated experience writing and filing SARs, including familiarity with FinCEN SAR forms and BSA/AML narrative-writing standards.
  • Experience with surveillance platforms (e.g., NICE Actimize, Nasdaq SMARTS, Eventus Validus, or similar) and blockchain analytical/KYT software; comfort partnering with engineering on custom/in-house surveillance logic, including hands-on experience with data stored on/processed via AWS S3, strongly preferred.
  • Strong SQL and data analysis skills; ability to query large trade/order datasets to investigate alerts and validate surveillance logic.
  • Strong analytical and investigative skills, with the ability to identify suspicious patterns, conduct detailed investigations, and make sound judgments based on available information.
  • Excellent written and verbal communication skills, with the ability to effectively interact with internal stakeholders, regulatory authorities, external parties, and customers.
  • Collaborative and team-oriented approach, capable of working with cross-functional teams and building strong relationships across the organization.
  • Experience with multi-asset class surveillance a strong plus, particularly any exposure to digital assets or novel/event-contract products.
  • Bachelor's degree required; advanced degree or certifications (e.g., CAMS – Certified Anti-Money Laundering Specialist, CFE) a plus.
Responsibilities
  • Design, build, and test surveillance scenarios/alerts across equities, options, futures, crypto, and prediction markets, covering manipulative and abusive trading patterns (e.g., spoofing, layering, wash trading, front-running, marking the close, insider trading, cross-product/cross-market manipulation, uneconomical trading).
  • Tune and validate surveillance thresholds and models; document methodology, coverage, and testing/back-testing results to demonstrate reasonable design under FINRA Rule 3110 and NFA Compliance Rule 2-9.
  • Conduct first- and second-level review of surveillance alerts and customer escalations; investigate potential violations of FINRA, SEC, NFA Compliance Rule 2-4 (Just and Equitable Principles of Trade), CFTC Rules 180.1/180.2, CEA Section 4c(a), and internal policies.
  • Conduct thorough investigations into suspicious transactions or activities, collaborating with Compliance, Legal, and Operations to gather necessary information and evidence.
  • Monitor cryptocurrency transactions and blockchain activity for signs of suspicious or illicit behavior, using blockchain analytical software to satisfy the firm's Know Your Transaction (KYT) requirements and identify potential risks.
  • Draft, review, and file Suspicious Activity Reports (SARs) arising from trade surveillance in accordance with BSA/AML requirements; maintain SAR documentation and related recordkeeping.
  • Report and escalate suspicious activities to appropriate regulatory or law enforcement agencies as required; prepare regulatory reporting and respond to inquiries, exams, and requests for information from FINRA, the SEC, and the CFTC/NFA.
  • Communicate with customers on monitoring and surveillance-related matters.
  • Partner with Compliance, Legal, and Technology teams to define requirements for new or enhanced surveillance tools, including vendor system implementation or in-house build.
  • Maintain and update Written Supervisory Procedures (WSPs) covering trade surveillance, market manipulation, and associated SAR filing across all product lines, including futures-specific procedures required under NFA Compliance Rule 2-9.
  • Monitor for emerging manipulation typologies specific to newer product types (e.g., crypto market abuse, prediction market-specific manipulation such as outcome manipulation or coordinated wash trading).
  • Coordinate with the CAT reporting team as needed to support surveillance investigations that rely on CAT data (CAT reporting itself is owned by a separate team).
  • Track and report key surveillance metrics (alert volumes, false-positive rates, SAR filing statistics, case aging) to senior management and committees.
  • Stay current on regulatory developments across FINRA, SEC, and CFTC/NFA affecting surveillance and AML obligations, and translate them into program and procedural updates.
  • Support general compliance initiatives, including procedural review and ad hoc projects.
Desired Qualifications
  • Series 24 is preferred.
  • Advanced degree or certifications (e.g., CAMS – Certified Anti-Money Laundering Specialist, CFE) a plus.
  • Experience with multi-asset class surveillance a strong plus, particularly any exposure to digital assets or novel/event-contract products.

Tastylive is a real-time online financial network that provides live streams, educational content, and actionable trade ideas for options, stocks, and futures. It streams over 100 original segments with more than 20 on-air traders, available seven days a week. The platform blends entertainment with education by delivering practical market insights and strategies from experienced traders. Its goal is to help traders navigate complex markets with confidence through reliable, timely information and ongoing support.

Company Size

51-200

Company Stage

Series C

Total Funding

$1B

Headquarters

Chicago, Illinois

Founded

2011

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Simplify Jobs

Simplify's Take

What believers are saying

  • Tastylive launched intraday margin coverage on June 4, 2026, expanding retail trading access.
  • The July 2026 show calendar stayed active, signaling daily programming and audience retention.
  • Free courses and over 120 segments keep top-of-funnel acquisition cheap and recurring.

What critics are saying

  • FINRA fined Tastytrade $850,000 on July 23, 2026 for best-execution failures.
  • FINRA fined Tastytrade $200,000 on June 2, 2026 for 71 unreported complaints.
  • Tastylive depends on personality-led education; Tom Sosnoff left in September 2025, weakening the franchise.

What makes Tastylive unique

  • Tom Sosnoff and ex-floor traders teach live options tactics seven days weekly.
  • Tastylive combines free streaming, courses, and brokerage distribution across YouTube, Roku, and Apple TV.
  • The brand owns niche credibility in probability-driven options education, not generic market commentary.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Mental Health Support

Commuter Benefits

401(k) Retirement Plan

Gym Membership

Paid Holidays

Paid Vacation

Paid Sick Leave

Wellness Program

Employee Stock Purchase Plan

Performance Bonus

Phone/Internet Stipend

Pet Insurance

Charitable Donation Matching

Flexible Work Hours