Tax Support Specialist

Tax Support Specialist 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 ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our team, and our mission. We 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, 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. We accept applications on an ongoing basis with no specified deadline. 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 a couple of times a year. All Checketeers gather in the spring for a required 3-day company offsite. 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.