Full-Time

Trade Desk Representative

Posted on 8/21/2026

Tastylive

Tastylive

51-200 employees

Real-time trading insights and education platform

Compensation Overview

$70k - $90k/yr

+ Performance bonus of 8-12%

Chicago, IL, USA

In Person

Five days on-site per week required.

Category
Customer Experience & Support (1)
Required Skills
Series 7
Salesforce
Customer Service

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Requirements
  • FINRA Series 3, 7, and 63 certification.
  • Familiarity with Regulation T and portfolio margin accounts.
  • Strong interpersonal skills and effectiveness in customer interactions, including the ability to identify appropriate solutions.
  • Extremely proficient with technology.
  • Experience with Salesforce, Slack, and Microsoft Teams.
  • Understanding of option execution mechanics and pricing.
  • Knowledge of futures and options on futures.
  • Ability to multitask in a fast-paced environment.
  • At least 2-3 years of experience in a similar high-call-volume role.
Responsibilities
  • Provide effective customer service to customers by applying detailed knowledge of retail brokerage services, trading software features and functionality, account management, and the trading platform.
  • Provide friendly, accurate, and efficient support via phone calls.
  • Assist customers with complex option order execution.
  • Analyze customer positions and explain the advantages and disadvantages of various strategies.
  • Work with customers to identify their needs as self-directed investors and provide timely solutions.

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