Trade Desk Representative, 24/7 Coverage

tastylive•Chicago, IL

6d•$90,000 - $95,000•Hybrid

About The Position

As a Trade Desk Representative, 24/7 Coverage at tastytrade, you will provide essential 24-hour trading support and risk monitoring for tastytrade customers during US market overnight hours and over the weekend. You will serve as the key weekend-day, swing, or overnight presence for 24-hour-traded products such as futures, futures options, SPX (GTH) index options, event contracts, and more. This role consists of a 4-day work week consisting of two 8-hour shifts during the week and two 12-hour shifts on the weekend. You must be comfortable working independently and handling positions or order-related inquiries, resolving trade disputes, reviewing customer risk, conducting customer risk callouts during risk events, and serving as the main point of contact for urgent customer issues during the shift. This role requires a deep understanding of the supported products, strong problem-solving skills under pressure, and the ability to make sound, independent decisions in a fast-paced environment.

Requirements

FINRA SIE, Series 7, 63, and 3 Certified
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
Proven track record working independently with minimal supervision in fast-paced environments
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
Strong interpersonal skills with the ability to build rapport and trust with customers during overnight or weekend hours
Excellent written and verbal communication skills across multiple channels (phone, email, chat)
Ability to explain complex derivatives and risk concepts clearly to customers with varying experience levels
Diplomatic approach when delivering difficult messages (margin calls, position liquidations, risk concerns)
Strong documentation skills for detailed shift handoff reports and incident summaries
Effective in customer interactions, especially in high-stress or volatile market environments
Extremely proficient with technology platforms, including Salesforce, Slack, Microsoft Teams, and Microsoft products
Ability to multitask effectively in a fast-paced environment with multiple customer inquiries simultaneously
Strong problem-solving abilities under pressure with limited resources and support during overnight hours
Excellent attention to detail for trade execution accuracy and risk monitoring
Comfortable troubleshooting technical issues and coordinating with support teams remotely

Nice To Haves

Previous experience in overnight or off-hours trading operations is a plus
Commitment to a minimum of one year in an overnight shift before potential transition to a day-shift role

Responsibilities

Provide support for all 24-hour and weekend-eligible instruments, including, but not limited to, outright futures, futures options, 24-hour stock trading, event contracts, GTH broad-based index options, and much more
Resolve trade disputes, execution errors, and order entry issues that occur 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, especially 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 (company-specific news, economic data, geopolitical developments, futures market moves)
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, especially any incoming transfers from customers experiencing a margin deficit
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

Benefits

Performance Bonuses
Stock Purchase Options
401k Plan
Medical/Dental/Vision Benefits
Continued Education Support
20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!)
10 Paid Sick Days
Gym Membership Reimbursement
Commuter Benefits
Pet Insurance
Wellness & Mental Health Programs
Charitable Donation Matching
Two Paid Volunteer Days Off
Daily catered lunch when in the office
Full kitchen with snacks and beverages
In-building gym
Shuttle to/from Metra