AI-Driven Tax Filing & Payments Associate (Remote)

Check; New York, San Francisco (NY, CA); Hybrid; USD 65,000 - 90,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Disability insurance (short/long)

Life insurance

Stock options

Flexible PTO & sick leave

Parental leave (16 weeks)

Return-to-work flexibility

9 holidays

401k plan

Internet stipend

Job summary

Check is rebuilding payroll infrastructure to power businesses that do payroll. As a Tax Filing & Payments Associate, you will own filing and payments for a defined set of agencies and employers, growing toward independent scope with senior support.

You'll collaborate across Payroll Operations, R&D, and Revenue, learning to prevent errors, document processes, and improve automation with AI. The role offers remote/hybrid options and a structured path toward ownership.

Qualifications

• 1–2+ years in operations, compliance, payroll, or related regulated/customer-facing function.
• Track record of picking up new systems/tools quickly, even without direct relevant past experience.
• Ability to own a defined piece of work and ask for help early when needed.
• Notice when something's off and raise it clearly for teammates.
• Genuine curiosity about AI and internal tooling; experience or eagerness to use AI.
• Strong written communication; able to log friction clearly for others.
• Comfort operating in a product still being built with ambiguity during ramp-up.

Responsibilities

• Take ownership of a defined set of jurisdictions with support from seniors — prep ahead of filing, original filings, and monitoring paid/late payments.
• File and pay under established workflows; learn how filing specs change with regulations.
• Help balance tax accounts and investigate escalations with senior teammates across Payroll Ops, R&D, and Revenue.
• Log friction points and write clear notes for the team to act on.
• Leverage AI to speed up work and improve accuracy as part of normal workflow.
• Manage your work within a defined scope; communicate deadlines and blockers; strive for improving SLAs.

Skills

Adaptability

Problem solving

Written communication

Curiosity about AI

Ownership

Attention to detail

Job description

Check is rebuilding payroll infrastructure to power businesses that do payroll. As a Tax Filing & Payments Associate, you will own filing and payments for a defined set of agencies and employers, growing toward independent scope with senior support.

You'll collaborate across Payroll Operations, R&D, and Revenue, learning to prevent errors, document processes, and improve automation with AI. The role offers remote/hybrid options and a structured path toward ownership.