AutoFile Specialist, Tax
WFA Digital Insight
Stripe’s Complex Tax Operations team is looking for an AutoFile Specialist who thrives on ambiguous, high‑stakes problems. Unlike routine tax support roles, this position sits at the crossroads of investigation, cross‑functional coordination, and process engineering, meaning every escalation you own becomes a chance to redesign the workflow that caused it. The job demands translating tangled data into clear action items and keeping leadership informed when issues require visibility. Because the team supports the TaxJar product, you’ll be dealing with real‑world tax filing anomalies that affect thousands of merchants, making the impact of each fix immediate and measurable. Candidates who enjoy digging into root causes and building reusable solutions will find the pace and purpose here compelling.
Job Description
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
How to Stand Out
- Highlight specific examples of complex escalations you resolved, focusing on the investigative process and outcome.
- Prepare a concise case study that showcases your Excel mastery—include formulas, pivot tables, or dashboards you built.
- Emphasize cross‑functional collaboration stories; interviewers value clear communication with product and engineering teams.
- Familiarize yourself with TaxJar’s core features and recent regulatory updates to demonstrate industry awareness.
- During the interview, ask about the current escalation workflow to show proactive thinking about process improvement.
- If offered, negotiate for a home‑office stipend or additional equity if the base salary isn’t disclosed.
- Watch for vague descriptions of responsibilities—seek clarification on reporting lines and decision‑making authority early in the process.
This is a remote position listed on WFA Digital, the platform for professionals who work from anywhere. Browse more remote jobs across all categories.