Full-Time

Trade Desk Representative

Coverage

Tastylive

Tastylive

51-200 employees

Real-time trading insights and education platform

Compensation Overview

$90k - $95k/yr

+ Discretionary performance bonus

Chicago, IL, USA

Hybrid

On-site in Chicago with potential hybrid remote based on experience.

Category
Finance & Banking (1)
Required Skills
Risk Management

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Requirements
  • FINRA SIE, Series 7, 63, and 3 certifications
  • Minimum 3-5 years of experience in high-volume customer service, trading operations, or a trade desk role
  • At least 3-5 years of hands-on experience with options, futures, and futures options trading
  • Overnight or off-hours trading operations experience is a plus
  • Deep understanding of futures and futures options execution mechanics, pricing, and market structure
  • Strong knowledge of options pricing models and determining exposure using Greeks
  • Experience with exchange-traded derivatives across multiple asset classes (equity index, commodities, rates, currencies)
  • Familiarity with extended hours stock trading including pre-market, 24-hour, and after-hours sessions
  • Understanding of Regulation T and portfolio margin account risk methodologies
  • Knowledge of futures contract specifications, margin requirements, settlement procedures, and SPAN margin methodologies
  • Strong risk management skills with the ability to identify and assess customer account risk exposures using the in-house risk screener (Sentinel)
  • Experience conducting customer risk callouts and discussing risk-reducing position adjustments in high-stress situations
  • Understanding of margin calculations, liquidation priorities, and portfolio risk metrics
  • Ability to analyze overnight risk events and their potential impact on customer positions
  • Familiarity with firm risk surveillance and unusual activity detection
  • Excellent interpersonal and communication skills for overnight or weekend hours
  • Documentation skills for detailed shift handoffs and incident summaries
  • Comfortable with technology platforms and coordinating with support teams remotely
Responsibilities
  • Provide support for all 24-hour and weekend-eligible instruments, including futures, futures options, 24-hour stock trading, event contracts, GTH broad-based index options, and more
  • Resolve trade disputes, execution errors, and order entry issues during weekend/overnight trading sessions
  • Analyze all customer positions and understand the potential risk involved
  • Work with customers to identify their needs as self-directed investors and provide timely solutions during risk events
  • Provide friendly, accurate, and efficient support via phone, email, or chat channels
  • Monitor customer account risk exposures during weekend and overnight trading sessions on all supported products, identifying accounts approaching or exceeding margin requirements
  • Perform proactive callouts to customers with potentially excessive risk or exposure from overnight risk events
  • Assist customers with managing excessive risk from overnight events, discussing position adjustments, hedging methods, or risk reduction options
  • Conduct real-time firm risk surveillance during overnight hours, monitoring for concentrated positions, unusual activity, or systemic risk concerns
  • Escalate critical risk situations to the tastytrade Margin and Risk team, providing detailed analysis and recommendations
  • Track and report unusual trading activity, account movements, or potential fraudulent behavior detected during overnight/weekend hours
  • Monitor overnight futures market volatility and liquidity conditions that may affect customer positions or firm risk
  • Assist customers with account management questions, including deposits, withdrawals, crypto transfer requests, and platform/account settings during overnight hours
  • Provide guidance on platform functionality across desktop, web, and mobile applications for overnight traders
  • Troubleshoot order entry issues, platform connectivity problems, and technical difficulties during overnight sessions
  • Educate customers on all 24-hour and weekend-eligible instruments regarding trading mechanics, margin requirements and methodologies, and risk management best practices
  • Escalate technical issues to Engineering or Technical Support teams, providing detailed documentation of customer problems
  • Serve as the primary point of contact for urgent customer issues during US overnight/early morning hours
  • Properly triage cases by coordinating with the US day-shift Margin & Risk teams on risk-related issues, providing detailed transition reports on overnight developments
  • Document overnight incidents, customer escalations, and operational issues with thorough detail for the following shift or day-shift follow-up
  • Provide detailed shift handoff reports summarizing overnight trading activity, risk events, customer issues, and action items
  • Contribute to the continuous improvement of overnight operations procedures, workflows, and customer communication protocols
  • Monitor overnight system performance and coordinate with Technology teams on platform issues or outages
  • Collaborate with Margin and Risk team on customer risk events
  • Coordinate with the Compliance/Fraud team on overnight trading surveillance alerts or suspicious activity
  • Work with the Banking team on overnight funding requests, wire transfers, or withdrawal issues requiring expedited processing
  • Work with reviewing, approving, and rejecting crypto wallets, including processing crypto deposits and withdrawals
  • Partner with the Engineering team to report platform bugs, execution issues, or system enhancements identified during overnight operations
  • Work independently with minimal supervision during overnight hours when senior leadership is unavailable
  • Make sound decisions on customer requests, risk situations, and operational matters using established policies and best judgment
  • Exercise discretion on when to escalate issues versus handling independently based on severity and complexity
  • Manage high-stress situations calmly and professionally, including upset customers, market volatility, and risk events

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