Technical Support Specialist

Company & Role

Company: tastytrade

Role:
Technical Support Specialist

Location:

Chicago, IL – In-Person (5 days/week)

Reports to:

Trade Desk Team Lead/Manager

Licensure

Required:

None

• Diagnose and resolve hardware and software issues across Mac, Windows, iOS, Android, and Linux.
• Troubleshoot platform access, login problems, two‑factor authentication, and connectivity issues.
• Resolve network problems, VPN configurations, firewall settings, and ISP conflicts.
• Assist with software installation, updates, and version compatibility.
• Troubleshoot display issues, multi‑monitor setups, data feeds, and order entry system errors.

• Provide friendly, professional support via phone, email, and chat.
• Guide customers through troubleshooting steps using clear, verbal instructions tailored to their skill level.
• Document all interactions thoroughly in Salesforce.
• Manage multiple support channels while maintaining high‑quality service.
• Escalate complex issues to Trade Desk Representatives or Engineering when needed.

• Assist with platform navigation, customization, and workspace optimization.
• Guide users through settings, preferences, and configuration options.
• Help customers transition seamlessly between desktop, web, and mobile platforms.

• Create detailed JIRA tickets for bugs, feature requests, and functionality issues.
• Document technical issues with reproduction steps, screenshots, and error messages.
• Identify patterns in customer issues and communicate systemic problems to Engineering.
• Test platform updates in staging environments.
• Collaborate with Product Content team to improve help documentation.

• 1‑3 years in customer service, support, help desk, or technical support role.
• Experience supporting users across multiple operating systems and devices.
• Familiarity with ticketing systems (JIRA, Confluence, Salesforce) preferred.
• Financial services or trading platform experience a plus but not required.
• Genuine curiosity and drive to learn about financial services.

• Strong proficiency with Mac, Windows, iOS, and Android operating systems.
• Understanding of networking concepts (DNS, IP addressing, ports, firewalls, VPNs).
• Knowledge of web browsers (Chrome, Safari, Firefox, Edge) including settings and developer tools.
• Familiarity with monitors, cables (HDMI, Display Port, USB‑C, Lightning), and peripherals.
• Ability to read error logs and diagnostic information.

• Exceptional verbal and written communication skills.
• Ability to explain technical concepts clearly to non‑technical users.
• Active listening, patience, and empathy with frustrated customers.
• Strong analytical and systematic troubleshooting approach.
• Detail‑oriented with excellent documentation skills.
• Adaptable and quick learner.

• Proficient with Salesforce, Microsoft 365, JIRA, and Slack.
• Remote support tools for screen sharing.
• Fast typing skills (minimum 50 WPM).

• Performance Bonuses
• Stock Purchase Options
• 401k Plan
• Medical/Dental/Vision Benefits
• 20 Paid Vacation Days (plus an additional 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

$55,000 – $65,000 (based on experience and qualifications)

Discretionary performance bonus: 5‑10% of base salary based on individual and company performance.

Our team is dedicated to building a diverse, inclusive, and authentic workplace. If your experience doesn't align perfectly, we encourage you to apply anyway.