Check

Building at Check At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. 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 out the full story | Tune in. Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. Our Team 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. About the Role Check is hiring a Strategic Initiatives Lead to run at our most important, ambiguous problems and turn them into durable solutions. This role is about getting to the heart of a problem quickly, cutting through noise and defining what actually matters. We’re looking for someone who approaches problems creatively, seeking out the simplest solutions and pulling on a variety of tools to get the job done: product changes, engineering fixes, operational processes, AI workflows and skills, or process design from scratch. You’ll partner closely with our COO and work across the company on problems that don’t fit neatly into a single function: from how we plan and forecast our operational teams, to rethinking complex, operationally heavy workflows through an AI-first lens. Many of these problems have a technical edge — analyzing data, working with AI tools, and understanding the underlying data models and systems you’re operating on. Some problems will require building from first principles, others will require connecting dots across teams and systems that don’t yet speak clearly to each other. The problems on our team don't come with playbooks. They come with real stakes, messy edges, and teams counting on you to figure it out. This is a role for a leader, but it’s also hands-on by design. You'll get to own things end-to-end: the strategy, the people management, and the work itself. You’ll be expected to operate with a high level of autonomy and willingness to get deep into the weeds to build real domain understanding. You’ll toggle between strategy and execution, helping the organization move faster, operate more simply, and adapt as priorities evolve. And as you solve each hard thing, new ones will emerge for you to take on. The scope here grows as you do, which means there's plenty of interesting territory ahead. What you’ll do - Get deep before you build — before proposing a path forward, you'll be expected to understand the mechanics of an issue from the ground up. That means working support tickets directly, solving tax notices, updating configurations, filing with agencies, and getting into the data until you know what's actually broken and why. - Turn ambiguity into a plan — structure the problem clearly, quantify the impact, identify root causes, and build a sequenced action plan. You'll write the brief, run the analysis, and make a crisp recommendation — not just flag that something is hard. - Own strategic programs end-to-end — from problem definition through execution and measurement, working across engineering, product, operations, and revenue teams. That includes standing up a monthly business review for your initiative: the right metrics, the right decisions surfaced, stakeholders aligned. - Launch and lead new teams — define the mission, hire the first people, build the processes, and develop leaders so the team eventually runs without you. You're building something to last. - Design how the work gets done — own workflow design and process engineering for your initiatives. Write the SOPs, build the playbooks, and create operating models that scale. You'll reach for AI-native solutions first — not as an add-on, but as the default starting point when you're designing how a team or process should work. - Develop your people — set clear expectations, give real feedback, and build an environment where strong performers grow. You're accountable for the output of your team, not just your own. What We're Looking For - You've built something from nothing — stood up a new team, function, or program in a high-growth environment and made it self-sustaining - You hold a high bar — for yourself, your team, and the work. You'd rather slow down and get it right than ship something half-baked - You simplify — you can take a messy, ambiguous problem and distill it into a clear problem statement and action plan - You're deeply curious — you ask "why" five times, you dig into the data, you talk to the people closest to the problem before forming an opinion - You've actually shipped AI into team operations — not just talked about it. You’re familiar with modern AI tools (LLMs, agents, copilots) and deploying them. - You're a strong people leader — you hire well, develop people, set clear expectations, and create environments where high performers thrive - You're comfortable working across engineering, product, ops, and business teams without needing a formal mandate Must have - 2+ Years of management experience - 7+ years of total experience in business operations, strategy, consulting, or a closely adjacent function - Demonstrated experience scoping and launching net-new teams or programs (0→1) - Comfortable working directly with data — SQL proficiency or equivalent analytical depth - Experience deploying AI tools into operational workflows (not just familiarity) Nice to have - Experience in payroll, fintech, or infrastructure/platform businesses - Background in management consulting, business operations, or program management What we offer: For full-time employees, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also offer stock options, flexible PTO and sick leave, up to16 weeks of fully paid parental leave for all new parents, flexible return-to-work arrangements, 9 annual holidays, a 401(k) retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. The actual annual salary for this role depends on each candidate's experience, qualifications, and location of work. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team's compensation. - The expected range in San Francisco, New York, Los Angeles, and Seattle is between $205,000 - $235,000. - The expected range for all other locations is between $174,500 - $200,000. #li-remote We accept applications on an ongoing basis with no specified deadline. 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.

Building at Check At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. 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 out the full story | Tune in. Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. Our Team 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. 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 and Office Policy: We build best when we come together on level ground. The Check team is distributed across the US, with offices in New York City and San Francisco. While we embrace remote work, 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 in the 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 company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also offer stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents, flexible return-to-work arrangements, 9 annual holidays, a 401(k) retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. The actual annual salary for this role depends on each candidate's experience, qualifications, and location of work. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team's compensation. - The expected range in San Francisco, New York, Los Angeles, and Seattle is between $92,500 and $101,750. - The expected range for all other locations is between $78,500 and $86,350. #li-remote We accept applications on an ongoing basis with no specified deadline. 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.

Building at Check At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. 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 out the full story | Tune in. Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. Our Team 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. 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. We accept applications on an ongoing basis with no specified deadline. 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.

Building at Check At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. 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 out the full story | Tune in. Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. Our Team 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. The Work At Check, you’ll combine strong engineering fundamentals with a drive to build software that meaningfully improves how payroll businesses operate. Our platform powers the movement of money, tax calculations, and compliance workflows for thousands of businesses, and much of the work we do involves turning complex infrastructure into clear, reliable systems for operators and partners. Our engineering team builds using cloud-native tools managed through infrastructure-as-code. We run a Python modular monolith that applies the principles of distributed systems while preserving the simplicity and ownership benefits of a mono-repo. Our systems rely on traditional HTTP APIs and durable asynchronous workflows to orchestrate everything from moving money to filing taxes. In this role, you’ll work across a wide range of problems, building software that helps Check move quickly and better serve partners and internal teams. Some work will be part of larger engineering commitments, while other opportunities will come from the ever-evolving needs of the business: a partner request, an internal tool improvement, a workflow that needs optimization, or a product gap slowing things down. If you enjoy building context quickly, running at problems, and shipping useful things, you’ll do well here. This role is ideal for someone with strong engineering fundamentals, high agency, and an entrepreneurial mindset. You might see yourself founding a company one day, or you may simply be energized by joining a growth-stage company where you can learn the business deeply while solving real problems across engineering, product, and operations. At Check, our engineers are close to the core of our business. This role offers the chance to see how decisions are made in a growth-stage company, and to develop the judgment that turns messy real-world problems into shipped software. In this role, you will: - Build and ship software that improves how partners, operators, and internal teams run payroll businesses on top of Check - Contribute to longer term engineering objectives while also adding immediate value by solving small friction points that improve our product and workflows - Take real ownership of your work from technical approach through implementation, rollout, and follow-through - Learn how complex production systems operate, from money movement and tax filings to the internal tools that support them - Work directly with engineers, product, and other teams across the company to understand partner and operator problems and develop practical solutions - Develop strong product and engineering judgment by seeing how technical decisions impact partners, operators, and the business - Build deep context across Check’s systems and workflows so you can recognize and get ahead of problems - Work in the open by sharing ideas, asking questions, and communicating clearly through code, documentation, and discussion - Readily receive feedback and mentorship to keep raising your own quality bar as an engineer Our Stack: - Python/Django for our API - React and TypeScript for our frontends - AWS and Terraform for our cloud infrastructure - Postgres for our database - Temporal for workflow orchestration - GitHub Tools for the job: - Strong software engineering fundamentals, with comfort working across backend and frontend systems - Proficiency in Python or Go; experience with Django, React, or TypeScript is a plus - Experience building product features, internal tools, or systems that solve real user or business problems - A high-agency, curious working style and excitement to learn and grow in a complex domain - Ability to navigate ambiguity, ask thoughtful questions, and turn context into action - Strong communication skills and a willingness to work closely with teammates and stakeholders across the business - A track record of following through, moving quickly, and taking pride in shipping useful, high-quality work Travel and Office Policy: Building Together on Common 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, time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team offsites, 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 company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also provide 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. The actual annual salary for this role depends 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. - In San Francisco, NYC, LA, and Seattle, the expected range is between $166,500 and $183,150. - For all other locations, the expected range is between $141,500 and $155,650. We accept applications on an ongoing basis with no specified deadline. 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.