Operations Specialist

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Sezzle

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2016

💳 Fintech

👥 B2C

🛍️ eCommerce

Fintech • B2C • eCommerce

Sezzle is a financial technology company that offers a "buy now, pay later" service, allowing consumers to purchase products and pay for them in four interest-free installments over six weeks. The Sezzle app provides users with a flexible financing alternative to traditional credit cards, enabling instant approval decisions without impacting credit scores. Sezzle partners with various top brands, including Amazon, Walmart, and Target, to offer in-app and in-store payment options. The company's mission is to empower consumers financially by providing more financial freedom and control. It is available as a mobile app, with millions of downloads and high user ratings, and works towards accessibility and inclusion on its platform.

📋 Description

• Serve as the escalation point for complex issues handed up from frontline support, owning them from investigation through resolution • Write and run SQL queries to investigate transaction discrepancies, refund and payment issues, reconciliation gaps, and other data-related problems • Use Claude and other AI tools to investigate issues, analyze logs, draft queries, and accelerate root-cause analysis • Trace issues across payment and support systems (e.g., card processors, ledgers, help-desk platforms) to identify where and why something went wrong • Reproduce, diagnose, and document root causes, then either resolve the issue directly or clearly hand off a well-scoped bug report to Engineering • Write clear, concise documentation, runbooks, and internal knowledge-base articles so recurring issues can be resolved faster • Partner closely with Engineering, Product, and Operations to escalate patterns, file detailed tickets, and follow issues through to a fix • Act as an advocate for both customers and frontline agents, surfacing trends and recommending improvements to our products, tooling, and processes

🎯 Requirements

• Hands-on SQL skills — comfortable writing queries with joins, filtering, and aggregation to investigate data independently (query optimization experience a plus) • Comfort using AI tools like Claude as part of a technical investigation workflow, with sound judgment about when to trust and how to verify their output • Strong analytical and troubleshooting instincts; you're driven to dig into the details of a system or process until you find the real cause • 3+ years of technical support, operations, or a related problem-solving role, ideally in software, fintech, or payments • Experience handling escalated, complex issues — troubleshooting, root-cause analysis, and problem resolution rather than scripted responses • Excellent written and verbal communication skills; able to explain technical findings clearly to both non-technical and engineering audiences • Able to manage multiple investigations at once and use personal judgment to prioritize and take initiative • Fluent in written and spoken English • A passion for what you do, paired with strong personal and corporate integrity, and genuine excitement to learn new technologies • Experience with Zendesk, Jira, Grafana/Loki, or similar support and observability tooling is a strong plus • Familiarity with payment systems, card processors, or ledger/reconciliation concepts is a plus.