Full-Time

Senior Manager

Fraud Investigations

Tastylive

Tastylive

51-200 employees

Real-time trading insights and education platform

Compensation Overview

$120k - $180k/yr

+ Performance Bonus + Stock Purchase Options

Chicago, IL, USA

Hybrid

Three days on-site per week required.

Category
Finance & Banking (1)
Required Skills
Series 7
Product Management
A/B Testing
Data Analysis

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Requirements
  • At least 7 years of fraud risk experience, including at least 3 years owning or leading a fraud function at a fintech, payments company, or digital brokerage.
  • A track record of hiring and developing fraud analysts.
  • Deep knowledge of automated clearing house fraud vectors, account takeover, and first-party fraud mechanics.
  • Experience with fraud analytics and data.
  • Strong vendor evaluation and management skills, including selecting, implementing, and replacing fraud tooling.
  • Experience defining key performance indicators and a fraud budget.
  • Ability to work cross-functionally with product, engineering, compliance, and legal while maintaining a position during conflicting-priority discussions.
  • Comfort operating in ambiguity and building structure where little exists.
  • Willingness to obtain Series 3, Series 7, and Series 63 or Series 66 licenses if not already held; tastytrade will sponsor and support the licensing process.
Responsibilities
  • Define tastytrade’s fraud taxonomy, risk philosophy, control framework, escalation protocols, and documentation.
  • Partner with the business to define the firm’s fraud risk appetite and translate it into a measurable fraud budget and key performance indicator framework; own reporting to senior leadership.
  • Design and document the escalation path for suspicious activity report filing decisions between the team and the anti-money laundering Officer.
  • Build and maintain the fraud universe map, including relevant vectors, where they occur in the customer journey, and current mitigation coverage.
  • Manage the fraud budget and headcount plan, including tooling and vendor spend.
  • Take strategic ownership of all fraud vectors across the customer lifecycle from account opening, funding, trading, and withdrawal.
  • Drive fraud investigations to resolution, coordinating with relevant internal and external partners.
  • Define and own the monitoring and detection strategy; evaluate potential vendors and partner with Product and Technology to ensure appropriate fraud-risk tools are in place.
  • Hire, build, and manage the Fraud Risk team; define role scopes, escalation authority, and relationships with Customer Support, Compliance, and Margin & Risk teams.
  • Own headcount planning and support incremental requests with demonstrated business value and strategic alignment.
  • Build the frontline escalation protocol with structured intake, defined triggers, and feedback loops.
  • Develop Fraud Investigator case playbooks and the settlement agreement process.
  • Build measurement infrastructure including labeled fraud data, false-positive-rate tracking, A/B testing capability, and trend analysis.
  • Own the fraud incident taxonomy and conduct retroactive recoding of existing records.
  • Evaluate alert calibration across active alert types, retire ineffective controls, and implement missing controls.
  • Deliver monthly reporting on fraud program performance to senior leadership and IG Group in partnership with the Enterprise Risk Manager.
  • Serve as the decision maker on fraud control changes and partner with Product and Technology to design fraud controls into new product launches.
  • Coordinate with Compliance and Margin & Risk teams on shared surveillance boundaries and escalation.
  • Advise Chief Compliance Officers on the fraud program’s interface with anti-money laundering compliance obligations.
Desired Qualifications
  • Knowledge of Bank Secrecy Act and Financial Crimes Enforcement Network regulations and suspicious activity report requirements, Financial Industry Regulatory Authority Rules 3310 and 3110, National Automated Clearing House Association rules, Securities and Exchange Commission Rule 15c3-3, and net capital rules.
  • Certified Fraud Examiner certification.
  • Demonstrated experience building or materially scaling a fraud program.

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