Overnight Weekend Engineer Jobs in Chicago, IL (NOW HIRING)

Company Name: tastytrade
Role: Trade Desk Representative, 24/7 Coverage
Location: Initially on-site and may be hybrid/remote based on experience
Reports to: Trade Desk Team Lead
Licensure Required: FINRA Series 7, 63, and 3 Certified

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.

What you'll do:
Trading Support & Execution

• 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

Risk Monitoring & Customer Protection

• 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

Platform Support & Technical Assistance

• 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

Operations & Incident Management

• 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

Cross-Functional Collaboration

• 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

Independent Decision-Making & Problem Solving

• 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

Who you are:
Experience & Credentials

• 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
• Previous experience in overnight or off-hours trading operations is a plus
• Proven track record working independently with minimal supervision in fast-paced environments
• Commitment to a minimum of one year in an overnight shift before potential transition to a day-shift role

Product & Trading Knowledge

• 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

Risk Management Expertise

• 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

Communication & Interpersonal Skills

• 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

Technical & Operational Skills

• 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

Company Perks + 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