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ABOUT CHECK Payroll 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! https://app.notion.com/p/checkhq/The-Generalist-Check-Solving-the-150-Billion-Payroll-Problem-3b24274a2e75804e9141cfac60476d25?source=copy_link 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. https://www.checkhq.com/partners 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. -- 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.

Listed by Check for a position based in the United States. Employers on this board attest they are hiring domestically.

Customer Service

133 days ago

Partner Support Lead, Tax

Check · United States, United States

Pay

$102k–138k

Setting

Remote

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ABOUT CHECK Payroll 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! https://app.notion.com/p/checkhq/The-Generalist-Check-Solving-the-150-Billion-Payroll-Problem-3b24274a2e75804e9141cfac60476d25?source=copy_link 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. https://www.checkhq.com/partners ABOUT THIS ROLE Check makes paying and filing taxes simple, enabling our partners to build best-in-class payroll businesses. The Tax Support team is core to that promise: working through tax notices, getting on the phone with agencies when needed, and making sure partners always know where things stand. As Partner Support Lead for our team managing tax notices, you will become a player/coach in the area. The people on your team bring years of payroll tax experience to the work; your job is making sure they can do their best with it. If you've spent years being the person everyone goes to, running the client relationship, owning the hard escalation, onboarding the new hire, but haven't had the title to match, this role is designed for exactly that transition. We're deliberately looking for operators with startup instincts over domain expertise, and we'll invest in the rest. IN THIS ROLE, YOU WILL: - Run the team's operating rhythm: stand ups, queue visibility, escalation paths, and cross-functional coordination - Learn the work well enough to step in on coverage gaps, complex escalations, or situations where a senior hand is needed - Help shape how the team operates: documentation, workflows, escalation paths, communication standards - Identify patterns across the team's work and bring forward recommendations, not just observations - Partner directly with the head of the department as a thought partner on team strategy, resourcing, and operational decisions TOOLS FOR THE JOB The ideal candidate will have: - 4-6+ years in operations or client service. - Startup or high-growth company background. - A track record of informal or formal people management. You've been the person others come to, and you know how to move a team without always having formal authority. - Strong communication skills. You can translate between team-level detail and leadership-level framing, and you know which audience needs which version. - A genuine learner. You'll be getting fluent in a niche domain on the job, and you find that interesting rather than uncomfortable. Nice to have’s: - Fintech experience is a plus, and payroll or tax background sets you apart. 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. -- 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.

Listed by Check for a position based in the United States. Employers on this board attest they are hiring domestically.

Customer Service

160 days ago

Tax Support Specialist

Check · United States, United States

Pay

$83k–108k

Setting

Remote

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ABOUT CHECK Payroll 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! https://app.notion.com/p/checkhq/The-Generalist-Check-Solving-the-150-Billion-Payroll-Problem-3b24274a2e75804e9141cfac60476d25?source=copy_link 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. https://www.checkhq.com/partners THE WORK At Check, we make paying and filing taxes seamless, enabling our partners to build best-in-class payroll businesses. As a Tax Support Specialist, you own a portfolio of tax agencies from end to end — meaning you're the person who knows them, handles what comes in from them, communicates on their behalf to partners, and gets resolution across the finish line. This role will own end-to-end tax workflows. When a tax notice is received, a filing needs completed, or a partner has a tax question they can't untangle, it ends with you. You build fluency with your agencies, their quirks, their timelines, their preferred escalation paths and use that knowledge to drive fast, accurate outcomes for the partners who depend on us. IN THIS ROLE, YOU WILL: - Own a defined set of federal, state, and local tax agencies end-to-end, including notice resolution, correspondence, corrections, and ongoing compliance across your portfolio - Be the direct point of contact with agencies: picking up the phone, navigating agency processes, and following through until issues are fully resolved - Communicate directly with partners about what's happening with their notices or tax accounts — translating complex agency interactions into clear, honest updates - Balance and reconcile tax accounts within your agency portfolio, surfacing discrepancies and driving resolution - Manage a queue of tax issues across your agencies, balancing urgency and complexity without losing track of what's open - Recognize when patterns in your portfolio point to a larger systemic issue and bring that signal to the right people TOOLS FOR THE JOB The ideal candidate will have: - 3–5 years of experience in payroll tax, tax operations, compliance, or notice resolution — with meaningful exposure to both agency communication and operational/filing work - Genuine comfort on the phone with tax agencies and in writing to partners — you're clear, professional, and don't over-promise - Experience with federal (IRS/SSA), state, and local agencies; ability to research and navigate unfamiliar ones when they come up - Organized and methodical — you can carry a portfolio of open issues across multiple agencies without things slipping - You solve first, escalate thoughtfully, and own outcomes through to completion - A curiosity for the edge cases; unfamiliar notice types feel like puzzles, not blockers 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. -- 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.

Listed by Check for a position based in the United States. Employers on this board attest they are hiring domestically.

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