Senior Product Designer

Payroll is broken. Come fix it alongside a team that's as passionate as you are! At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We view problems to solve and jobs to be done as opportunities to contribute to the solution; we ignore conventional role boundaries in favor of the unique strengths and value each builder brings to our team and to our mission.

Join us if you're ready to roll up your sleeves and redefine payroll. Let's simplify the complex, make a real impact, and create a better future for businesses of every size.

Today, many 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.

Check's embedded infrastructure powers payroll platforms that pay millions of employees, all controlled through Check Console: our software layer used to manage 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 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.

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 design, or a similar role designing complex software 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 both systems thinking and strong visual design craft
• 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

For full-time employees, Check offers stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave for new parents, flexible return-to-work, 9 annual holidays, 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.

Check is a payroll platform that redefines how people get paid and makes it easier for payroll businesses to launch, grow, and thrive. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive. Check is a springboard for building and scaling payroll businesses, offering a platform that simplifies complex workflows and creates intuitive user experiences. The company is committed to fostering a collaborative and innovative environment where designers can impact the industry through thoughtful design and user-centric solutions.