Technical Support Specialist Chicago, IL

Company: tastytrade Role: Technical Support Specialist Location: Chicago, IL – In-Person (5 days/week) Reports to: Trade Desk Team Lead/Manager Licensure Required: None As a Technical Support Specialist with tastytrade, you will be the frontline expert for resolving technical and platform-related issues for our customers. You will assist traders via phone, email, and chat with everything from basic website navigation and software installation to complex troubleshooting of hardware, operating system, and connectivity issues across multiple platforms (desktop, web, mobile). Your role is critical in ensuring customers can access and utilize our trading technology seamlessly, enabling them to focus on their trading strategies rather than technical obstacles. You will serve as the bridge between customers and our Engineering team, documenting bugs, feature requests, and system improvements while providing exceptional technical support. Responsibilities Technical Troubleshooting 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 Customer Support 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 Platform & User Education 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 Engineering Collaboration 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 Qualifications Experience 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 Technical Skills Strong proficiency with Mac, Windows, iOS, and Android operating systems Understanding of networking concepts (DNS, IP addressing, ports, firewalls, VPNs) Familiarity with monitors, cables (HDMI, DisplayPort, USB-C, Lightning), and peripherals Ability to read error logs and diagnostic information Communication & Problem-Solving 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 Tools & Benefits Proficient with Salesforce, Microsoft 365, JIRA, and Slack Remote support tools for screen sharing Performance Bonuses Stock Purchase Options 401k Plan 20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday) 10 Paid Sick Days Pet Insurance Wellness & Mental Health Programs Charitable Donation Matching Daily catered lunch when in the office Full kitchen with snacks and beverages Shuttle to/from Metra Office located in the West Loop – Chicago's growing center of tech, great cuisine, and high-end bars Salary Salary Range: $55,000–$65,000. The actual salary offered will be based on the candidate's level of experience and qualifications. Discretionary performance bonus: 5–10% of base salary based on individual and company performance. Equal Employment Opportunity As set forth in tastytrade’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. #J-18808-Ljbffr tastylive, Inc.