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, tastylive, 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 tastylive 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 success by the value we create for our users.
Location: Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars.
tastytrade | tastylive | tastyfx | tastycrypto
1330 W Fulton Market, Chicago, IL 60607
*Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they have every single qualification. Our team is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role but your experience doesn't align perfectly, we encourage you to apply anyway. You may be just the right candidate for this or other roles!