Technical Product Manager, Infrastructure and Dev Ops

Department: Product 

Reports To: Head of Product

Employment Type: Full-Time 

Location: Chicago, IL – In-Person

Salary: $132,000 – $160,000 

About the Role

tastytrade is a self-directed brokerage built for active options and futures traders, with a platform spanning web, desktop, and mobile. In order to meet the demands of our product's growth, we're hiring a Senior Product Designer to drive foundational elements: build the token architecture, component system, and craft standards the whole organization moves on. This is foundational work with platform-wide impact in a regulated financial environment where design decisions carry operational weight alongside UX tradeoffs. 

We're looking for someone who leads with craft and thinks in systems. You'll work across our core platform, raise the craft bar across the team, and help build the design foundation that lets us scale quickly without accumulating debt. 

What You'll Do:

• Own design execution across the core platform (web, desktop, and mobile) from early discovery through production handoff 

• Set and hold a high craft standard across the team: precise visual execution, complete interaction states, clear information hierarchy, and appropriate motion. When you review work, you give specific feedback with a clear rationale, not general impressions 

• Build and maintain design system foundations: shared token layer, component architecture, usage guidelines, and the conventions that keep the platform feeling coherent as it scales 

• Partner with engineering on implementation quality: you care how the product shows up to real customers, not just whether the Figma file was polished before handoff 

• Establish shared navigational conventions and design standards that vertical product teams build within 

• Produce documentation thorough enough that other designers can build on your decisions without needing you in the room 

• Work directly with PMs and engineers to define scope and make calls under ambiguity 

• Mentor other designers on craft, systems thinking, and technical execution: invest in how they think through problems and grow their capabilities 

Who You Are:

• 8+ years of product design experience, with at least 2 years working in a regulated financial environment: fintech, trading, banking, crypto, investing, etc. 

• A track record of moving metrics: you can point to specific design decisions you owned that shifted a meaningful outcome and explain the reasoning behind them 

• Experience building or significantly contributing to a design system in a product org: tokens, component architecture, the decisions that let a team scale without accumulating debt 

• High bar for visual craft in complex, data-dense interfaces: you bring the same rigor to a 40-column data table that others bring to a hero screen, and your portfolio demonstrates that visual quality and usability reinforce each other 

• Systems thinking applied to design: you understand why a component decision matters at scale and can build foundations other designers extend without breaking 

• Strong feedback and mentoring instincts: you can articulate what's wrong and why, and make the work better without taking over 

Preferred Qualifications 

• Background in options, futures, or equities trading products specifically 

• Experience with token-based workflows and design-to-code handoff at a component level 

• Crypto or emerging asset class product experience 

• Performance Bonuses 
• Stock Purchase Options 
• Medical/Vision/Dental Benefits 
• 401k Plan 
• 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