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 - Own high-risk, cross-functional escalations that do not have a clear playbook - Ensure timely follow-through and closure on issues, decisions, and action items - Investigate recurring issues and identify root causes - Partner cross-functionally to remove blockers and prevent repeat failures - Bring clarity to ambiguity by connecting people, data, and context - Serve as an escalation partner for issues requiring leadership visibility, root cause thinking, or coordinated resolution - Support operational readiness and respond quickly to external changes impacting the organization - Provide visibility into friction points, risks, and remediation strategies - Help improve the operator and user experience through prevention, mitigation, and resolution 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: You translate complex analysis into insights that drive decisions - Collaborative partner: You work effectively with operations teams, product, and leadership - Curious investigator: You naturally ask "why" and don't stop until you understand what's really happening - Systems thinker: You see how operational pieces connect and look for leverage points for improvement - Builder 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 improvement - 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 with AI, automation, or workflow tools to improve organizational effectiveness - Understanding of operational workflows (filing processes, user operations, risk management) - Experience in tax operations, sales tax automation, financial services, or regulated environments - 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