Technical Support Specialist

tastytrade•Chicago, IL

5h•$55,000 - $65,000•Onsite

About The Position

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.

Requirements

1-3 years in customer service, support, help desk, or technical support role
Experience supporting users across multiple operating systems and devices
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, DisplayPort, 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)

Nice To Haves

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

Responsibilities

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

Benefits

Performance Bonuses
Stock Purchase Options
401k Plan
Medical/Dental/Vision Benefits
20 Paid Vacation Days (plus an additional paid vacation 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
Office located in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars