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Stripe

Autofile Specialist, Tax

Stripe
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remote senior full-time Toronto, ON

First indexed 24 Jun 2026

Description

Job Description

We're looking for an AutoFile Specialist, Tax to manage high-stakes, ambiguous escalations and pave the way for stable operational growth. In this role, you will tackle the challenges that don't have a pre-written playbook,investigating complex anomalies, identifying why they occurred, and coordinating across teams to ensure they don't happen again.

Responsibilities

  • Manage complex escalations: Own high-risk, cross-functional issues, ensuring timely resolution and closure.
  • Investigate root causes: Conduct deep-dive analyses into recurring operational problems to distinguish systemic issues from isolated incidents.
  • Drive operational visibility: Provide insights into friction points and mitigation strategies using metrics and reporting.
  • Partner cross-functionally: Collaborate with operations, product, and leadership to resolve operational blockers and advocate for permanent solutions.
  • Navigate ambiguity: Connect relevant people, data, and context to bring clarity to unstructured situations.
  • Support operational readiness: Prepare for external regulatory or system changes to support new capabilities.
  • Elevate the experience: Improve operator and user experiences through strategic prevention and resolution frameworks.

Requirements

  • 3+ years of experience in high-growth operations, escalation management, or process improvement.
  • Proven ability to resolve complex, unstructured issues logically.
  • Exceptional prioritization skills with ability to manage multiple high-stakes tasks efficiently.
  • Excellent communication and collaboration skills, particularly with non-technical audiences.
  • Comfort working in ambiguous and high-accountability environments.

Preferred Qualifications

  • Experience in tax operations, sales tax automation, financial services, or regulated environments.
  • Understanding of operational workflows, including filing processes and risk management.
  • Experience working with product or engineering teams to automate tools and processes.
  • Familiarity with root cause analysis or continuous improvement methodologies (e.g., Lean, Six Sigma).
  • Experience collaborating with operations leads and senior stakeholders on strategy alignment.
This listing is enriched and indexed by YubHub. To apply, use the employer's original posting: https://job-boards.greenhouse.io/stripe/jobs/7997545