Sezzle is looking for a Billing Specialist: Dispute Resolution & Back Office Operations who thrives on investigative work and complex problem-solving. In this role, you'll be the backbone of our billing integrity, ensuring accuracy and consistency behind the scenes.
What You'll Do
- Review invoices, rental agreements, and account activity for accuracy.
- Audit charges including fees, damages, tolls, fuel, late returns, and administrative costs.
- Generate reports for customer-facing agents.
- Correct billing errors and adjust charges when appropriate.
- Ensure billing follows internal policy, contractual terms, and regulatory requirements.
- Process billing updates, credits, and account corrections within internal systems.
- Maintain accurate account notes and documentation.
- Investigate customer billing disputes and formal complaints.
- Gather, analyze, and submit supporting documentation to challenge disputes.
- Determine validity of disputes using company policy and available evidence.
- Prepare written responses explaining billing decisions clearly and professionally.
- Issue credits, partial adjustments, or uphold charges with supporting rationale.
- Coordinate with Claims, Operations, Customer Support, and Compliance teams when needed.
- Track and manage dispute queues to meet service level agreements (SLAs).
- Handle escalated cases from customer support.
- Respond to chargebacks and payment disputes.
- Prepare documentation for financial partners or payment processors.
- Identify trends in recurring disputes and recommend process improvements.
- Assist with reporting and reconciliation tasks.
- Support audits and compliance documentation requests.
What We're Looking For
- 1–3+ years experience in billing, accounting support, claims, fraud review, chargebacks, or back-office operations.
- Strong analytical and problem-solving skills.
- Excellent written communication skills (this role is heavily email/documentation based).
- High attention to detail and organization.
- Ability to review contracts and apply policy to real-world scenarios.
- Comfortable working in multiple systems and spreadsheets.
- Ability to manage a queue and meet deadlines.
- High school diploma or equivalent.
Nice to Have
- Experience in rental car, mobility, insurance, fintech, or subscription billing environments.
- Chargeback or payment processor dispute experience.
- Claims handling or damage review experience.
- Familiarity with Zendesk, Salesforce, Stripe, or similar platforms.
- Experience reviewing documentation such as invoices, photos, and repair estimates.
- Post-secondary education in business, communications, customer service, or a related field.
- Prior experience in customer support, fleet operations, logistics, automotive services, call center operations, or collections.
- Experience working with vendors, service providers, or third-party platforms.
Technical Stack
- Zendesk
- Salesforce
- Stripe
Team & Environment
You will coordinate with Claims, Operations, Customer Support, and Compliance teams.
Benefits & Compensation
- Compensation: $6.00 - $8.00 USD hourly.
Work Mode
This is a fully remote position.
Whip is proud to be an equal-opportunity employer committed to providing equal employment opportunities to all employees and applicants and prohibits discrimination and harassment of any type without regard to protected characteristics.
