Overnight Trade Desk Representative Chicago, IL

Position: Overnight Trade Desk Representative New Chicago, IL Company Name: tastytrade Role: Overnight/Swing Shift Trade Desk Representative Location: On-site to start, transitioning to 3 days/week in office (manager-determined). Remote work considered for experienced candidates outside Chicagoland/NW Indiana. Reports to: Head of Client Brokerage Services Licensure Required: FINRA SIE, Series 7 and 63 Certified + FINRA Series 3 preferred (or willing to obtain within 60 days of start date) As an Overnight Trade Desk Representative at tastytrade, you will be responsible for providing essential 24‑hour trading support and risk monitoring for tastytrade customers during US market overnight hours. You will serve as the key overnight presence for futures and futures options, extended‑hours and 24/5 stock trading, cryptocurrencies, customer position risk, firm risk, and fraud surveillance. You will also work on the forefront of newly released products that trade around‑the‑clock. You must be comfortable with working independently and handling various position and order‑related inquiries, resolving trade disputes, conducting customer risk callouts for overnight risk events, and acting as the main point of contact for urgent customer issues during overnight and early morning hours. This role requires a deep understanding of derivatives, strong problem‑solving skills under pressure, and the ability to make sound independent decisions in a fast‑paced environment. Available Shifts: Standard shift is 10pm‑7am (must be open to swapping to the swing (5pm‑2am) to cover for sick/vacay coverage or if we need to shift due to volume)

• Overnight Shift: Sunday ‑ Thursday (to Friday Morning), 10:00 PM ‑ 7:00 AM CT
• Swing Shift: Sunday ‑ Thursday (to Friday Morning), 5:00 PM ‑ 2:00 AM CT

What You’ll Do Trading Support & Execution

• Support futures, futures options, 24‑hour broad‑based index options, and 24‑hour stock trading (extended hours and overnight sessions)
• Handle complex multi‑leg orders and resolve execution errors
• Analyze customer positions and identify risk exposure
• Monitor customer account risk during overnight sessions, identifying accounts approaching margin deficiencies or potential excessive risk
• Perform proactive callouts to customers with excessive risk from overnight events (news events, economic data, geopolitical developments)
• Conduct real‑time firm risk surveillance for concentrated positions or unusual activity
• Escalate critical situations to Margin and Risk team with detailed analysis

Operations & Problem Solving

• Serve as primary contact for urgent overnight customer issues
• Provide detailed shift handoff reports on trading activity, risk events, and action items
• Work independently with minimal supervision, making sound decisions using established policies
• Coordinate with Technology, Compliance, Banking, and Margin teams on overnight incidents

Platform & Technical Support

• Assist with account management, deposits, withdrawals, and crypto transfers
• Troubleshoot order entry, connectivity, and technical issues
• Educate customers on trading mechanics and risk management

Who You Are

• FINRA SIE, Series 7, 63, and 3 Certified
• 3‑5 years in high‑volume customer service, trading operations, or trade desk role
• 3‑5 years of hands‑on experience with options, futures, and futures options
• Deep understanding of derivatives execution, pricing models, and Greeks
• Proven ability to work independently with minimal supervision
• Experience conducting risk callouts in high‑stress situations
• Knowledge of Regulation T, portfolio margin, and SPAN methodologies
• Familiarity with extended hours trading (pre‑market, 24‑hour, after‑hours)
• Excellent communication skills across phone, email, and chat
• Proficient with Salesforce, Slack, and Microsoft Products

Personal Attributes

• Self‑motivated with strong ownership and accountability
• Calm under pressure during market volatility and crisis situations
• Diplomatic when delivering difficult messages (margin calls, liquidations)
• Flexible and adaptable to changing overnight market conditions
• Committed to an overnight schedule (Sunday‑Thursday) with a minimum 1‑year commitment before day‑shift consideration
• Overall dependable and trustworthy individual
• Performance Bonuses
• Stock Purchase Options
• 40…

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