Autofile Specialist, Tax

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. About the team The Complex Tax Operations team supports the TaxJar product and broader Tax Operations and Delivery teams by increasing operational effectiveness. The team resolves complex operational issues and escalations while helping the organization to support new capabilities before they scale. What you’ll do 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. You will work at the intersection of problem-solving, cross-functional collaboration, and process improvement to bridge the gap between initial friction and long-term operational resilience. This role is ideal for someone who loves diving headfirst into unstructured problems, connecting the dots between isolated operational issues, and bringing order, clarity, and repeatability to chaotic situations. 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. Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement. • Clear communicator: Ability to translate complex analysis into actionable insights. • Collaborative partner: Effective working relationships with operations, product, and leadership teams. • Curious investigator: Proactive in asking "why" to fully understand issues. • Systems thinker: Ability to see operational connections and identify improvements. • Builder mindset: Develop infrastructure for team self-sufficiency in answering questions. Minimum requirements • Strong operations, escalation management, or process improvement experience • Proven ability to investigate complex issues and drive them to resolution • Ability to manage multiple priorities with urgency and accuracy • Excellent communication and cross-functional collaboration skills • Comfort working in ambiguity and high-accountability environments Preferred qualifications • Experience in tax operations, financial services, or regulated operational environments • Understanding of operational workflows (filing processes, user operations, risk management) • Background working closely with operations or product teams to improve processes • Familiarity with root cause analysis and continuous improvement methods • Experience partnering with operations leads and senior stakeholders