AutoFile Specialist, Tax

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. 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 Own high-risk, cross-functional escalations that do not have a clear playbookEnsure timely follow-through and closure on issues, decisions, and action itemsInvestigate recurring issues and identify root causesPartner cross-functionally to remove blockers and prevent repeat failuresBring clarity to ambiguity by connecting people, data, and contextServe as an escalation partner for issues requiring leadership visibility, root cause thinking, or coordinated resolutionSupport operational readiness and respond quickly to external changes impacting the organizationProvide visibility into friction points, risks, and remediation strategiesHelp improve the operator and user experience through prevention, mitigation, and resolution 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: You translate complex analysis into insights that drive decisionsCollaborative partner: You work effectively with operations teams, product, and leadershipCurious investigator: You naturally ask "why" and don't stop until you understand what's really happeningSystems thinker: You see how operational pieces connect and look for leverage points for improvementBuilder mindset: You don't just answer questions—you build infrastructure so teams can answer their own Minimum Requirements 3+ years of experience in high-growth operations, escalation management, or process improvementProven ability to investigate complex issues and drive them to resolutionAbility to manage multiple priorities with urgency and accuracyExcellent communication and cross-functional collaboration skillsComfort working in ambiguity and high-accountability environments Preferred Qualifications Experience with AI, automation, or workflow tools to improve organizational effectivenessUnderstanding of operational workflows (filing processes, user operations, risk management)Experience in tax operations, sales tax automation, financial services, or regulated environmentsFamiliarity 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 role is available either in an office or a remote location (35+ miles or 56+ km from a Stripe office). In-office expectations Office-assigned Stripes spend at least 50% of the time in a given month in their local office or with users. This hits a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility about how to do this in a way that makes sense for individuals and their teams. Working remotely at Stripe A remote location is defined as being 35 miles (56 kilometers) or more from one of our offices. While you would be welcome to come into the office for team/business meetings, on-sites, meet-ups, and events, our expectation is you would regularly work from home rather than a Stripe office. Stripe does not cover the cost of relocating to a remote location. We encourage you to apply for roles that match the location where you currently live or plan to live.