Role: Software Engineer (Ruby) Location: Chicago, IL - Hybrid Salary: $130,000-$150,000As a Software Engineer you will be part of a team that builds out the technology powering our retail brokerage business and supporting our other business initiatives. We care about the speed and stability of our back-end systems as much as we care about the customer-facing applications we build. Our architecture is distributed and consistently evolving as our business grows and we face different technical challenges, but always with a focus on practicality and performance.
You'll help by modifying existing systems, taking ownership of current systems as well as green field projects, and troubleshooting issues as they arise. Our engineers work with a plethora of tools including Java, Javascript, and Ruby. You'll work primarily in Ruby but will have opportunities to expand your skill set into areas where your interests and our technology intersect.
Ruby doesn't have to be your primary language today. If you're strong in another object-oriented language - Java, for example - and you're genuinely keen to make Ruby your day-to-day, we'd like to hear from you. Our technical interview is conducted in Ruby wherever possible, so you'd need to be comfortable enough to code in it by the time we meet.
What You'll Do - Work in multiple languages across different parts of the tastytrade stack and/or front-end trading client applications.
- Design, build and maintain services in a distributed architecture, thinking about failure modes, latency and data consistency as you go.
- Provide guidance and leadership to more junior members of the team when questions arise about language or implementation specifics, and contribute in a meaningful way to our peer review process.
- Translate requirements and technical direction into production-quality code with lightweight guidance from a senior engineer or team leadership.
- Work independently on smaller-scope tasks, as well as under the guidance of senior engineers to contribute to larger projects.
- Write comprehensive tests for your code.
- Engage in light infrastructure work to support application development work where applicable.
- Continue your growth by learning new systems and working towards ownership of tastytrade's systems.
Who You Are - Demonstrable professional experience working as a software engineer on a team.
- A mastery of at least one of our languages or frameworks and experience dealing with it in a production context.
- Minimum 2 years of professional experience with Ruby - or equivalent experience in another object-oriented language (e.g. Java) alongside a commitment to work primarily in Ruby and to interview in it.
- Experience building or operating distributed systems.
- The ability to learn quickly in areas in which you don't already have deep expertise.
- A willingness to learn new languages, frameworks, or technologies beyond your current expertise.
- Accountability and a willingness to take ownership of your work.
- Curiosity and a proactive approach to problem-solving.
Nice to Have - Experience writing Ruby outside of Rails.
- Front-end experience, ideally with Svelte, and any exposure to micro-frontend architectures.
- A working grasp of application security and secure coding practices.
How We Work We try to take a thoughtful approach to our ways of working as a company. We follow a hybrid working model with 3 days in the office - which we think balances the need to collaborate effectively and connect with each other. When it comes to how we deliver, there are 5 things we want everyone to do to drive high performance, better learning and career satisfaction:
- Lead and Inspire: Drives trust, alignment, and enthusiasm.
- Think Big: Focus on the problems that most impact commercial outcomes.
- Champion the Client: Understand and prioritise clients' needs.
- Deliver at Pace: Push for fast, sustainable growth.
- Raise the Bar: Take ownership, be accountable and share feedback.
Who you are: Experience & Credentials - FINRA SIE, Series 7, 63, and 3 Certified
- Minimum 3-5 years of experience in high-volume customer service, trading operations, or a trade desk role
- At least 3-5 years of hands-on experience with options, futures, and futures options trading
- Previous experience in overnight or off-hours trading operations is a plus
- Proven track record working independently with minimal supervision in fast-paced environments
- Commitment to a minimum of one year in an overnight shift before potential transition to a day-shift role
Product & Trading Knowledge - Deep understanding of futures and futures options execution mechanics, pricing, and market structure
- Strong knowledge of options pricing models and determining exposure using Greeks
- Experience with exchange-traded derivatives across multiple asset classes (equity index, commodities, rates, currencies)
- Familiarity with extended hours stock trading, including pre-market, 24-hour, and after-hours sessions
- Understanding of Regulation T and portfolio margin account risk methodologies
- Knowledge of futures contract specifications, margin requirements, settlement procedures, and SPAN margin methodologies
Risk Management Expertise - Strong risk management skills with the ability to identify and assess customer account risk exposures using the in-house risk screener (Sentinel)
- Experience conducting customer risk callouts and discussing risk-reducing position adjustments in high-stress situations
- Understanding of margin calculations, liquidation priorities, and portfolio risk metrics
- Ability to analyze overnight risk events and their potential impact on customer positions
- Familiarity with firm risk surveillance and unusual activity detection
Communication & Interpersonal Skills - Strong interpersonal skills with the ability to build rapport and trust with customers during overnight or weekend hours
- Excellent written and verbal communication skills across multiple channels (phone, email, chat)
- Ability to explain complex derivatives and risk concepts clearly to customers with varying experience levels
- Diplomatic approach when delivering difficult messages (margin calls, position liquidations, risk concerns)
- Strong documentation skills for detailed shift handoff reports and incident summaries
- Effective in customer interactions, especially in high-stress or volatile market environments
Technical & Operational Skills - Extremely proficient with technology platforms, including Salesforce, Slack, Microsoft Teams, and Microsoft products
- Ability to multitask effectively in a fast-paced environment with multiple customer inquiries simultaneously
- Strong problem-solving abilities under pressure with limited resources and support during overnight hours
- Excellent attention to detail for trade execution accuracy and risk monitoring
- Comfortable troubleshooting technical issues and coordinating with support teams remotely
Discretionary Performance Bonus: 8-12% of base salary based on individual and company performance.
Company Perks + Benefits: - Medical/Dental/Vision Benefits
- Continued Education Support
- 20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!)
- Gym Membership Reimbursement
- 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
Location: Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars.
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!
