Senior Product Designer

About this role

Today, 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 experience
• Solve complex payroll problems through deep research and design thinking, shaping everything from interaction models to product architecture
• Conduct user research — including direct conversations with payroll operators and platform partners — to uncover insights and inform design decisions
• Identify opportunities to rethink existing product patterns and drive improvements that make Check's infrastructure products significantly more intuitive and efficient for operators
• Partner closely with engineering and product leaders to design surfaces and workflows that simplify the complex realities of payroll operations
• Elevate the visual and interaction design of existing product surfaces to create a more cohesive, intuitive, and delightful experience
• Prototype and iterate quickly on new ideas, incorporating feedback from users and cross-functional teams
• Contribute to the evolution of Check’s product design standards and help raise the overall bar for design across the company
• Collaborate with marketing and creative teams to socialize platform enhancements to existing partners and future prospects

Many 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 products
• Strong UX instincts and the ability to simplify complex systems, workflows, and data-heavy interfaces
• Experience designing workflow-driven products or operational software (fintech, developer tools, enterprise platforms, or similar)
• A portfolio demonstrating strong systems thinking, elevated visual design taste, and judgment around AI application
• Experience collaborating closely with engineering teams and designing within technical constraints
• Ability to independently drive ambiguous design problems from discovery through shipped product
• Experience conducting or leading user research and translating insights into product improvements
• Experience designing for multi-step workflows and complex user journeys
• Comfort working in fast-moving environments where designers often own broad problem spaces
• Strong communication skills and the ability to clearly articulate design decisions and tradeoffs

Travel & Office Policy

The 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.