Operations Specialist

About Sezzle: 

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role:

We are seeking a talented and motivated Operations Specialist to join our Operations team — someone with both a high IQ and a high EQ who thrives on getting to the bottom of complex problems. This role sits behind the frontline support team, handling escalated issues that require deeper investigation into our systems and data. You'll spend your days querying databases, tracing transactions across payment platforms, and using AI tooling like Claude to diagnose root causes and resolve issues that others can't. It's a great fit for a curious, technically-minded problem solver who wants to grow at the intersection of operations, data, and engineering within a fast-paced, rapidly growing team.

What You'll Do:

• 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

• 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

About You:

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

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