Jobs › tastytrade

Trade Desk Representative

tastytrade · Chicago, IL · $70,000–$90,000 a year · tt - Trade Desk

Posted Aug 21, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you helped someone with a complex technical issue under time pressure.

What they are checking: Whether they can stay accurate and helpful when customers need fast answers during market hours.

How do you stay accurate when you're handling many calls back to back?

What they are checking: Whether they have habits that prevent errors in a fast-paced phone role.

What would you do

A customer wants to close a multi-leg options position that's partly filled. How would you help them on the phone?

What they are checking: Whether they can guide complex option order execution clearly and accurately.

A customer asks what strategy they should use for an earnings play. How do you respond?

What they are checking: Whether they explain pros and cons of strategies without crossing into recommendations for a self-directed client.

A frustrated customer says the platform caused them to lose money. How do you handle the call?

What they are checking: Whether they stay calm, gather facts and escalate properly without admitting fault prematurely.

A customer asks you to place a trade for them over the phone. What do you do?

What they are checking: Whether they know the firm's procedures for phone orders and verification.

About the work

Explain the difference between a Reg T margin account and portfolio margin to a customer.

What they are checking: Whether they understand both margin types as the posting requires.

Walk me through the advantages and disadvantages of a covered call versus a cash-secured put.

What they are checking: Whether they can analyze positions and explain strategy tradeoffs clearly.

What happens when an options position is assigned early, and how would you explain it to a customer?

What they are checking: Whether they understand assignment risk and can make it clear to customers.

How does your Series 3, 7 and 63 knowledge help you on calls?

What they are checking: Whether their licenses reflect working knowledge of futures, options and state rules.

Practice this interview out loud.

Offer builds a real interview for this exact role at tastytrade from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by tastytrade.

Company&nbsp;Name:&nbsp; tastytrade Role:&nbsp; Trade Desk Representative - Inbound Phone Representative/Inbound Chat and Email Representative Location:&nbsp; Chicago, IL – In-Person &nbsp; Licensure Required:&nbsp; FINRA Series 3, 7, and 63 Certified &nbsp; As&nbsp; a Trade Desk Representative&nbsp;with ta stytrade ,&nbsp; you will&nbsp;be responsible for&nbsp;providing effective customer service for tastytrade customers by&nbsp;utilizing&nbsp;sharp, in-depth knowledge of all retail brokerage services. This would include trading software features and functionality, account management, and any other questions about the tastytrade platform.&nbsp;&nbsp; &nbsp; What&nbsp;You’ll&nbsp;Do: &nbsp; &nbsp; • Work schedule: Monday - Friday, 7 AM - 4 PM or 8 AM - 5 PM, depending on staffing needs &nbsp; &nbsp; • Provide friendly,&nbsp;accurate, and efficient support via phone calls&nbsp; &nbsp; • Assist&nbsp;customers with complex&nbsp;option&nbsp;order execution&nbsp; &nbsp; • Analyze customers positions and provide advantages and disadvantages for various strategies&nbsp; &nbsp; • Work with customers to&nbsp;identify&nbsp;their needs as self-directed investors and provide solutions&nbsp;in a timely manner&nbsp; &nbsp; Who&nbsp;You&nbsp;Are: &nbsp; &nbsp; • Comfortable commuting to the office 5 days/week&nbsp; &nbsp; • FINRA Series 3, 7, and 63 Certified &nbsp;&nbsp; &nbsp; • Familiar with Regulation T and portfolio margin accounts&nbsp; &nbsp; • Strong interpersonal skills, effective in customer interactions, and ability to identify&nbsp;appropriate solutions&nbsp; &nbsp; • Extremely proficient with use of technology&nbsp; &nbsp; • Salesforce, Slack, Teams&nbsp; &nbsp; • Understanding of&nbsp;option&nbsp;execution mechanics and pricing&nbsp; &nbsp; • Knowledge of futures and options on futures&nbsp; &nbsp; • Ability to multitask in a fast-paced environment&nbsp; &nbsp; • At least 2-3 years of experience in a similar role with high call volume Company Perks + Benefits: &nbsp; • Performance Bonuses &nbsp; • Stock Purchase Options &nbsp; • 401k Plan &nbsp; • Medical/Dental/Vision Benefits &nbsp; • Continued Education Support &nbsp; • 20 Paid Vacation Days (plus an&nbsp;additional&nbsp;paid vacation&nbsp;day&nbsp;the month of your birthday!) &nbsp; • 10 Paid Sick Days &nbsp; • Gym Membership Reimbursement &nbsp; • Commuter Benefits &nbsp; • Pet Insurance &nbsp; • Wellness & Mental Health Programs &nbsp; • Charitable Donation Matching &nbsp; • Two Paid Volunteer Days Off &nbsp; • Daily catered lunch when in the office &nbsp; • Full kitchen with snacks and beverages &nbsp; • In-building gym &nbsp; • Shuttle to/from Metra &nbsp; Salary Range: &nbsp;$70,000 - $90,000&nbsp; &nbsp; The actual salary offered will be based on the candidate's level of experience and qualifications &nbsp; Discretionary performance bonus: &nbsp;8-12%&nbsp;of &nbsp;base salary based on individual and company performance&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; About IGNA&nbsp;+ tasty &nbsp; IG North America is home to tastytrade,&nbsp;tasty live & &nbsp;tastyfx—a family of brands built to democratize trading and empower individual investors. Founded in Chicago by the creators of thinkorswim, acquired by London-based IG Group in 2021, we combine startup innovation with the backing of a FTSE 100 fintech&nbsp;operating&nbsp;across five continents serving over 1.3m customers and handling billions of dollars in transactions – built on scale, trust, and proof. <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":1,"335551620":1,"335557856":16777215,"335559738":0,"335559739":330}">&nbsp; From our headquarters in Chicago's Fulton Market, our team builds award-winning trading platforms, produces live financial education content daily, and creates technology that makes complex markets accessible. tastytrade is our retail brokerage for self-directed investing and trading, with&nbsp;tasty live providing content to educate our customers. tastyfx is the fastest-growing forex broker in the US.&nbsp; We're&nbsp;a lean, collaborative team that values autonomy, pragmatism, and impact. Whether&nbsp;you're&nbsp;building technology, creating content, serving customers, or supporting operations,&nbsp;you'll&nbsp;work alongside people who are passionate about disrupting traditional finance and genuinely care about helping traders succeed. Our culture rewards initiative, embraces experimentation, and measures success by the value we create for our users.&nbsp; The bar is high – bring a curious and forward-thinking&nbsp;mindset&nbsp;and&nbsp;we'll&nbsp;give you the platform to define what comes next. Join us at IG|tasty – the future gets built here. &nbsp; &nbsp; Location:  Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars.&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":1,"335551620":1,"335557856":16777215,"335559738":0,"335559739":330}">&nbsp; tastytrade &nbsp;|&nbsp; tasty live   |&nbsp; tastyfx &nbsp; 1330 W Fulton Market, Chicago, IL 60607  &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":1,"335551620":1,"335557856":16777215,"335559738":0,"335559739":330}">&nbsp; *Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they have every single qualification. Our team is dedicated to building a diverse, inclusive, and authentic workplace, so if&nbsp;you’re&nbsp;excited about this&nbsp;role,&nbsp;but your experience&nbsp;doesn’t&nbsp;align perfectly, we encourage you to apply anyway. You may be just the right candidate for this or other roles!  <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":1,"335551620":1,"335557856":16777215,"335559738":0,"335559739":330}">&nbsp;

Apply at tastytrade