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About Sezzle

Sezzle is on a mission to empower the next generation financially by revolutionizing the shopping experience through advanced technology and interest-free installment plans. We aim to innovate beyond payments by enhancing how customers discover, engage with, and purchase products, ultimately boosting merchant sales through increased conversions and higher average order values. As we advance in fintech and retail innovation, we seek dynamic individuals passionate about creating not just transactions but unique shopping experiences.

Role Overview

We are looking for a skilled Operations Specialist to join our team, someone with strong analytical and emotional intelligence who enjoys solving complex challenges. This position works behind frontline support to manage escalated cases needing detailed system and data examination. Daily tasks include running database queries, tracking transactions across payment platforms, and leveraging AI tools such as Claude for root cause investigation and resolution. It's an ideal role for a curious, technically inclined problem solver eager to grow at the intersection of operations, data, and engineering within a fast-growing environment.

Key Responsibilities

Act as the escalation lead for difficult issues from frontline support, managing them from analysis to resolution.
Create and execute SQL queries to explore transaction irregularities, payment and refund concerns, and reconciliation discrepancies.
Employ AI tools like Claude to support troubleshooting, analyze logs, formulate queries, and speed up root cause identification.
Trace problems through payment and support systems such as card processors, ledgers, and helpdesk platforms to pinpoint failure points.
Reproduce, diagnose, and document root causes before directly fixing or handing off detailed bug reports to Engineering.
Develop clear documentation including runbooks and internal knowledge-base articles to facilitate efficient resolution of repeated issues.
Collaborate with Engineering, Product, and Operations departments to highlight patterns, create detailed tickets, and ensure issue resolution.
Represent customers and frontline agents by identifying trends and recommending improvements in products, tools, and processes.

Qualifications and Skills

Proficient with SQL including joins, filters, and aggregations independently; query optimization knowledge is advantageous.
Experience utilizing AI tools like Claude for technical problem investigations, with a discerning approach to trust and verification of outputs.
Strong analytical mindset with a passion for diagnosing system and process issues until the root cause is found.
Minimum of 3 years in technical support, operations, or related roles, preferably in software, fintech, or payments.
Proven ability to manage escalated, complex problems through investigation, root cause analysis, and resolution, beyond scripted solutions.
Excellent written and oral communication skills, capable of explaining technical concepts clearly to both technical and non-technical stakeholders.
Ability to juggle multiple investigations concurrently, prioritize effectively, and demonstrate initiative.
Fluency in written and spoken English.
A strong passion for the work, integrity, and eagerness to acquire new technical knowledge.
Experience with tools like Zendesk, Jira, Grafana/Loki is highly desirable.
Familiarity with payment systems, card processors, and ledger/reconciliation concepts is a bonus.

Personal Attributes

Maintain exceptionally high standards, continuously raising the bar and ensuring that issues are fixed thoroughly so defects do not recur.
Innovative and unbounded by traditional methods, thriving on developing new approaches.
Action-oriented, valuing speed and decisive risk-taking when appropriate.
Earns trust through active listening, candid communication, and respectful interactions.

Compensation

The monthly gross salary range for this position is $1800 to $2700 USD.

Operations Specialist