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This position has closed. tastytrade removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Senior Product Designer, I

tastytrade · Chicago, IL · $132,000–$160,000 a year · tt - UX and Product Management

Posted Sep 25, 2026 · We last checked this listing on Oct 5, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Walk me through a complex product problem you solved. What made it hard?

What they are checking: Whether they can work through genuinely hard design problems on their own.

Tell me about a time you worked independently with a PM and engineers without much direction.

What they are checking: Whether they can operate without scaffolding, which the posting stresses.

What would you do

How would you design an options order ticket on mobile so an active trader can build a multi-leg order quickly without mistakes?

What they are checking: Whether they can handle dense, high-stakes trading flows on a small screen.

How do you design for conversion on mobile without adding risky friction or dark patterns in a regulated product?

What they are checking: Whether they balance business goals with user safety and regulatory rules.

Engineering says your design will take three times as long as planned. How do you respond?

What they are checking: Whether they can find a simpler path without losing the core value.

About the work

How much do you know about options and futures trading, and how has that shaped your design work?

What they are checking: Whether they understand trading well enough to design for experienced traders.

How do you keep a design consistent across web, desktop and mobile while respecting each platform?

What they are checking: Whether they can maintain one product experience across very different surfaces.

How would you test a new trading feature with users before launch?

What they are checking: Whether they use research with real traders instead of guessing what they want.

How do you design error states for something like a rejected order?

What they are checking: Whether they think through failure cases, which matter a lot when money is involved.

How would you measure whether your mobile redesign improved conversion?

What they are checking: Whether they connect design work to measurable business outcomes.

Practice this interview out loud.

Offer builds a real interview for this exact role at tastytrade from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by tastytrade.

Department: Product &nbsp; Reports To: Head of Product Employment Type: &nbsp;Full-Time &nbsp; Location:&nbsp; Chicago, IL – In-Person Salary : $132,000 – $160,000 &nbsp; &nbsp; About the Role tastytrade&nbsp;is a self-directed brokerage built for active options and&nbsp;futures&nbsp;traders, with a platform spanning web, desktop, and mobile.&nbsp;We're&nbsp;hiring a Senior Product Designer to work alongside our trading design team and significantly raise the quality of our mobile trading experience:&nbsp;tastytrade's&nbsp;largest and fastest-growing customer surface, and the area with the most direct line between focused design investment and meaningful conversion improvement. This role&nbsp;operates&nbsp;at the intersection of complex financial product design and a regulated environment where decisions carry real operational weight. &nbsp; We're&nbsp;looking for a Senior Product Designer who understands trading, can work through genuinely hard product problems, and can&nbsp;operate&nbsp;independently alongside a PM and engineering team. This is not a role for someone who needs a lot of scaffolding. &nbsp; &nbsp; What You'll Do: <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"> Own design for complex trading features across web, desktop, and mobile from problem definition through ship: order flows, portfolio views, risk management tools, real-time data surfaces &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"> Work as a peer with PMs and engineers, contributing to product direction rather than just executing it &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"> Participate in discovery: user research, usability testing, and data review are part of how you form and defend design decisions, not an afterthought &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="4" data-aria-level="1"> Design for iteration: propose A/B tests, set up measurable experiments, and use results to inform the next move &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="5" data-aria-level="1"> Communicate design decisions clearly to designers and non-designers alike: run critiques, present rationale to leadership, align cross-functional teams &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="6" data-aria-level="1"> Give substantive feedback and contribute to a consistent product experience across the team &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="7" data-aria-level="1"> Connect your work to business outcomes: understand&nbsp;and be able to speak to&nbsp;how design affects conversion, retention, and engagement &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="8" data-aria-level="1"> Mentor other designers on product thinking, domain knowledge, and navigating complex problem spaces &nbsp; &nbsp; Who You Are: <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"> 8+ years of product design experience, with at least 3 years in a regulated financial environment&nbsp;(trading, brokerage, crypto, banking, investing,&nbsp;etc) &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"> A track record&nbsp;of moving metrics: you can point to specific design decisions&nbsp;you owned&nbsp;that shifted conversion, retention, or engagement, and explain how you got there &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"> Strong mobile app design background: you have shipped native iOS or Android and understand what makes mobile a distinct design challenge &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="4" data-aria-level="1"> Visual craft suited to complex, high-stakes interfaces: you design for expert users who are time-pressured and low on tolerance for friction, and your work ships at the same quality it was designed &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="5" data-aria-level="1"> Able to drive projects forward without heavy direction: you figure out what is needed, pull in the right people, and keep things moving &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="6" data-aria-level="1"> Bring strong product thinking to every project: collaborate closely with PMs and engineers as a peer, ask the right questions before execution starts, push back constructively when something&nbsp;doesn't&nbsp;serve users, and&nbsp;know&nbsp;when to commit and execute &nbsp; Preferred Qualifications: <span data-ccp-props="{"134245418":true,"134245529":true,"335559738":360,"335559739":240,"335572079":6,"335572080":0,"335572081":0,"469789806":"single"}">&nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"> Direct experience with options, futures, or equities trading products &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"> Experience designing for crypto trading or other emerging asset classes &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"> Familiarity with real-time data, high-density&nbsp;interfaces&nbsp;and the constraints they create &nbsp; Company Perks + Benefits: • Performance Bonuses&nbsp; • Stock Purchase Options&nbsp; • Medical/Vision/Dental Benefits • 401k Plan&nbsp; • 20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!)&nbsp; • 10 Paid Sick Days&nbsp; • Gym Membership Reimbursement&nbsp; • Commuter Benefits&nbsp; • Pet Insurance&nbsp; • Wellness & Mental Health Programs&nbsp; • Charitable Donation Matching&nbsp; • Two Paid Volunteer Days Off&nbsp; • Daily catered lunch when in the office&nbsp; • Full kitchen with snacks and beverages&nbsp; • In-building gym&nbsp; • Shuttle to/from Metra&nbsp; Discretionary Performance Bonus:&nbsp; 8-12% of base salary based on individual and company performance. &nbsp; About IGNA + tasty IG North America is home to tastytrade, tasty live , and tastyfx—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 FTSE 100 fintech operating across five continents serving over 1.3m customers and handling billions of dollars in transactions – built on scale, trust, and proof. 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. 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. The bar is high – bring a curious and forward-thinking mindset and we'll give you the platform to define what comes next. Join us at IG|tasty – the future gets built here. Location:  Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars. tastytrade | tasty live | tastyfx &nbsp; 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!