Senior Product Designer

About CheckPayroll is broken. It's still running on decades-old infrastructure. We're rebuilding it.We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive.On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story!Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners.About this roleToday, payroll platforms rely on archaic, utilitarian software to process payroll for thousands of businesses and ensure hundreds of thousands of workers are paid correctly and on time. Their work is high-stakes and deeply personal for each and every worker they pay, but the tools supporting them are stuck in the past, and make the process unnecessarily complex. This critical infrastructure in their business feels more like an operational obstacle than a product designed to help them succeed. At Check, we believe this software should be just as thoughtful, intuitive, and beautifully designed as the best consumer products on the market.Our software layer manages payroll complexities across thousands of businesses simultaneously. The opportunity ahead is to transform it into the best platform for operating a payroll business. A system that anticipates user needs, simplifies complex workflows, and turns operational software into genuinely delightful user experiences.We’re looking for a Senior Product Designer (& UX-pert) who enjoys untangling complex systems and shaping how sophisticated products work at a foundational level. This role is ideal for a designer who is excited by challenging, high-impact problems, and enjoys translating complicated workflows into elegant product experiences.You’ll engage directly with users to deeply understand their use cases and optimal workflows, and work closely with engineering, product, and design leadership to translate those insights into core product patterns. This role spans strategy, research, UX, and visual design, and offers the opportunity to redefine the design direction for an entire industry. Come join us as we set a new standard for how payroll management software should operate! In this role, you will:Own the end-to-end design of major enhancements within Check's products, from problem framing through shipped experienceSolve complex payroll problems through deep research and design thinking, shaping everything from interaction models to product architectureConduct user research — including direct conversations with payroll operators and platform partners — to uncover insights and inform design decisionsIdentify opportunities to rethink existing product patterns and drive improvements that make Check's infrastructure products significantly more intuitive and efficient for operatorsPartner closely with engineering and product leaders to design surfaces and workflows that simplify the complex realities of payroll operationsElevate the visual and interaction design of existing product surfaces to create a more cohesive, intuitive, and delightful experiencePrototype and iterate quickly on new ideas, incorporating feedback from users and cross-functional teamsContribute to the evolution of Check’s product design standards and help raise the overall bar for design across the companyCollaborate with marketing and creative teams to socialize platform enhancements to existing partners and future prospectsMany backgrounds could fit this role, but ideal candidates will have some or all of the following:6–10+ years of experience in product design, UX/UI research, UX/UI design, or a similar role designing complex software or infrastructure productsStrong UX instincts and the ability to simplify complex systems, workflows, and data-heavy interfacesExperience designing workflow-driven products or operational software (fintech, developer tools, enterprise platforms, or similar)A portfolio demonstrating strongsystems thinking, elevated visual design taste, and judgment around AI applicationExperience collaborating closely with engineering teams and designing within technical constraintsAbility to independently drive ambiguous design problems from discovery through shipped productExperience conducting or leading user research and translating insights into product improvementsExperience designing for multi-step workflows and complex user journeysComfort working in fast-moving environments where designers often own broad problem spacesStrong communication skills and the ability to clearly articulate design decisions and tradeoffsTravel & Office PolicyThe Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat. For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.--Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process.Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.Compensation Range: $153K - $198KLocationRemote; New York City, NY; San Francisco, CAEmployment TypeFull timeLocation TypeRemoteDepartmentSales & MarketingMarketingDeadline to ApplyAugust 31, 2026 at 7:00 AM UTCCompensationNYC, SF, LA, Seattle$180K – $198K • Offers EquityRemote US$153K – $168.3K • Offers EquityThe actual annual salary for this role is dependent on each candidate’s experience, qualifications, and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team’s compensation.Check is proud to offer employee benefits that support a healthy life outside of work for individuals of all backgrounds. Full-time team members have access to flexible PTO and sick leave, generous paid parental leave for all new parents and flexible return-to-work, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. We also provide high-quality medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on your first day of work.