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Tax Health Check Specialist

100% remote Flexible hours Hiring now

Toast is a technology company that assists restaurants and local businesses in succeeding in a digital environment. They are looking for a Tax Health Check Specialist who will act as a liaison between the tax operations team and customers, ensuring accurate and timely tax filings by resolving missing tax information and setting up state tax accounts.

Responsibilities

  • Conduct customer-facing meetings to review and collect missing tax registration information required for filing
  • Guide customers through the process of registering for state tax accounts they haven't yet established
  • Follow up persistently and professionally with customers to obtain outstanding documentation and credentials
  • Maintain accurate records of customer status, outstanding items, and resolved issues
  • Coordinate internally with Tax Filing, Tax Amendment, and Onboarding teammates to communicate customer readiness and flag blockers
  • Support broader Tax Operations processes as needed, including processing amendments, account audits, and case documentation
  • Escalate complex tax registration issues to senior team members with clear context and documentation

Skills

  • 1–2 years of experience in a customer-facing, operations, or administrative role
  • Strong written and verbal communication skills — you'll be talking to stressed restaurant operators regularly
  • Highly organized with strong follow-through; nothing falls through the cracks on your watch
  • Comfortable working independently and managing a queue of open customer cases
  • Basic familiarity with payroll taxes or willingness to learn quickly
  • Detail-oriented — accuracy in this role directly impacts customers' ability to file their taxes correctly
  • Prior experience with Salesforce or similar CRM tools is a plus
  • Experience with state tax agency portals or payroll platforms is a plus

Benefits

  • Cash compensation (overtime, bonus/commissions if eligible)
  • Equity
  • Benefits
  • Flexibility to meet Toasters’ changing needs
  • Hybrid work model that fosters in-person collaboration while valuing individual needs
  • Reasonable accommodations for persons with disabilities to enable them to access the hiring process

Company Overview

  • Toast is a point-of-sale and restaurant management platform designed for businesses in the food service and hospitality industry. It was founded in 2011, and is headquartered in Boston, Massachusetts, USA, with a workforce of 1001-5000 employees. Its website is https://pos.toasttab.com.
  • Company H1B Sponsorship

  • Toast has a track record of offering H1B sponsorships, with 3 in 2026, 26 in 2025, 32 in 2024, 39 in 2023, 66 in 2022, 29 in 2021, 17 in 2020. Please note that this does not guarantee sponsorship for this specific role.
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