Technical Support Specialist

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. What You'll Do: 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 Who You Are: 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) 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 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 Proficient with Salesforce, Microsoft 365, JIRA, and Slack Remote support tools for screen sharing Fast typing skills (minimum 50 WPM) Company Perks/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  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  About IGNA + tasty    IG North America is home to tastytrade, tasty live , tastyfx, and tastycrypto—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 global fintech leader with 50+ years of experience.   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 tasty live  providing content to educate our customers. tastyfx is the fastest-growing forex broker in the US. tastycrypto provides self-custody digital wallets for decentralized finance.   We're a lean, collaborative team that values autonomy, pragmatism, and impact. Whether you're building technology, creating content, serving customers, or supporting operations, you'll 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 succe