Software Engineer, Reconciliation & Reporting

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. The Role You will join the Recon and Reporting team, which owns our post-transaction systems: the platform responsible for reconciling money, tracing the end-to-end flow of funds, and meeting our tax and regulatory reporting obligations to merchants, customers, and authorities worldwide. Reconciliation and financial reporting are essential to running a payments business, and given our transaction volume, the projects you own will have direct, measurable impact on financial accuracy and trust. You will help build and operate the systems that ingest and integrate global card-network settlement and report files (Visa, Mastercard, and equivalents), along with data from acquirers, processors, and banks, and reconcile them against internal payment data to power settlement, dispute, cost, tax, and regulatory reporting. You will own well-scoped projects within this platform end-to-end, with guidance from more experienced engineers. Our vision is to make reconciliation and reporting accurate, automated, and near real-time. You Will • Own small, well-bounded projects end-to-end with guidance available: clarify requirements, design, build, test, ship, and follow up. • Build and maintain features within the ingestion and reconciliation pipelines that match card-network and partner reports against internal transaction data. • Contribute to tooling that provides end-to-end traceability of money throughout the system. • Develop features for reporting and reconciliation products that are accurate, reliable, timely, scalable, and user-friendly for both internal finance teams and external merchants. • Produce standardized journals and summaries that feed downstream accounting, audit, and analysis. • Contribute to our large-scale tax and regulatory reporting systems, including US IRS information returns (the 1099 family, issued at the scale of tens of millions of forms annually to merchants and customers) and international regimes such as EU-wide CESOP and country-specific reporting for Australia, Ireland, and Spain. • Support broader regulatory and compliance obligations (AML, KYC, and similar), with careful handling of sensitive and PII data, including TIN validation and secure form generation and filing. • Validate your work before calling it done, using code review, tests, small experiments, or usage signals, including for AI-assisted changes. • Take agency in debugging and escalating production issues across services, giving the team clear context on what changed, when it changed, how it changed, and what risk remains. • Collaborate with engineers, product managers, data analysts, and finance, tax, and compliance partners, contributing to technical design and product decisions that shape feature outcomes. • Review peers' work, apply their feedback to your own, and document learnings, including AI workflows the team can reuse. • Opportunistically improve the systems you touch when it fits your project scope, replacing manual and redundant work with automation, and route larger issues to the right owner. You Have • 3+ years of professional software or data engineering experience. • A Bachelor's degree in a technical field (Computer Science, Engineering, Mathematics, or similar) or equivalent technical experience. • Experience building or maintaining batch- or event-driven data pipelines, with exposure to workflow-orchestration technologies (e.g., Airflow, Temporal, Spark, or equivalent) and a working understanding of distributed systems. • Proficiency in at least one major programming language (e.g., Java, Python, Go) and solid SQL. • Experience delivering well-scoped projects or features end-to-end (design, build, test, ship, operate), with guidance from more experienced engineers. • Strong communication skills: you surface concerns alongside a concrete proposal, and you give teammates clear context when debugging and escalating. • Care for engineering quality, including maintainable and testable code, code review, CI/CD, and observability, appropriate for a complex, high-stakes financial environment. • Proficiency in using AI tools throughout the software development lifecycle, with the judgment to recognize where they accelerate work and where output needs additional validation. Nice to Have • Exposure to financial, tax, regulatory, or payments reporting and reconciliation products. • Familiarity with the payments ecosystem (merchants, acquirers, card networks, and issuers/processors), including authorization, clearing, and settlement, card-network settlement file formats, or ISO-8583. • Understanding of accounting principles, double-entry bookkeeping, and financial reconciliation processes. • Experience with cloud