Senior Product Designer

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.

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 product enhancements within Check Console, from problem framing through shipped experience

• Translate complex payroll systems into intuitive user experiences, shaping everything from interaction models to product architecture

• Partner closely with engineering and product leaders to design surfaces and workflows that simplify the complex realities of payroll operations

• Identify opportunities to rethink existing product patterns and drive improvements that make Console significantly more intuitive and efficient for operators

• Conduct user research — including direct conversations with payroll operators and platform partners — to uncover insights and validate design decisions

• 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 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

We build best when we come together on level ground:

The Check team is distributed across the US, and we have offices in New York City and San Francisco. While we embrace remote work, we believe time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team off-sites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat each spring.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays, and the team hosts regular happy hours, game nights, etc.

What we offer:

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.

At Check, transparency and fairness in compensation are our top priorities: our compensation bands are visible to all employees across all roles. The actual annual salary for this role is dependent on each candidate’s experience, qualifications, and work location:

• The expected range in San Francisco, NYC, LA, and Seattle is between $200,000 and $220,000.

  • The expected range for all other locations is between $180,000 and $198,000.