Billing Specialist: Dispute Resolution & Back Office Operations

*This is a remote position*

DriveWhip is a mobility provider in the Washington, DC area, with offices in multiple cities that Leases/Rents vehicles to Uber, Lyft and other On-Demand or Rideshare drivers. As a ground floor member of an exciting new company all associates will be tasked with a variety of responsibilities. An appreciation for the pros and cons of start up culture is a must.

Our goal is to deliver superior customer service, respect, expertise and responsiveness to our customers. As stewards of our company, you will be responsible for awarding every customer with a positive rental experience.

Position Summary:
We are seeking a detail-oriented Billing & Dispute Resolution Specialist to support our administrative and back-office billing operations. This role is responsible for reviewing account charges, investigating billing discrepancies, and resolving customer disputes accurately and efficiently.
This is not a traditional call-center collections position. Instead, this role focuses on billing operations and dispute/chargeback resolution — working behind the scenes to ensure invoices are correct, policies are applied consistently, and dispute win rates stay consistent with company goals.
The ideal candidate enjoys investigative work, problem-solving, and handling complex account scenarios that require analytical thinking and proficiency with spreadsheets and data review

Essential Duties and Responsibilities (include, but are not limited to the following):

• Billing Administration
  
  
  
  • Review invoices, rental agreements, and account activity for accuracy
  
  
  • Audit charges including fees, damages, tolls, fuel, late returns, and administrative costs
  
  
  • Report generation 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
    
    
  
  
  
  


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  Dispute Resolution (Primary Focus)

  
  
  
  
  • Investigate customer billing disputes and formal complaints
  
  
  • Gather, analyze, and submit supporting documentation (contracts, photos, text messages, rental contracts, etc.) 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)
  
  
  
  

  Back-Office Support

  
  
  
  
  • 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
  
  
  
  

Qualifications Required:

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  • 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
    
    
  
  
  
  

  Preferred Qualifications

  
  
  
  
  • 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
  
  
  
  

Education and Experience:

• High school diploma or equivalent required
  
  


• Post-secondary education in business, communications, customer service, or a related field preferred
  
  


• Prior experience in customer support, fleet operations, logistics, automotive services, call center operations, or collections preferred
  
  


• Experience working with vendors, service providers, or third-party platforms is a plus

Salary:  $5.00 - $7.00 USD hourly                                                                                                            

Work Environment:

Typical work environment includes desktop computing work using typical desktop computing equipment (laptop, keyboard, mouse, monitors, desk, chair) in an office environment and/or remote workspace environment.

Physical Demands:

• Ability to sit and use typical desktop computing workspace equipment - e.g. mouse, keyboard, monitor, phone - for extended periods of time.


• Manual dexterity to operate a typical desktop computing workstation.


• Ability to communicate both verbally and in writing, using virtual meeting and communication tools such as email, Google Meet, and Slack.


• Reasonable accommodations will be made for qualified individuals with disabilities.

Equal Employment Opportunity:

Whip is proud to be an equal-opportunity employer. Whip is committed to providing equal employment opportunities to all employees and applicants and prohibits discrimination and harassment of any type without regard to race, color, religion, sex (including gender, gender identity, gender expression, pregnancy, childbirth, breastfeeding status, or related medical conditions), age, sexual orientation, national origin, ancestry, marital status, military or veteran status, genetic information, disability (including physical or mental disability, medical condition, or medical leave), or any other characteristic protected by federal, state, or local law. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Consistent with our commitment to equal employment opportunity, Whip will make reasonable accommodations for qualified individuals with disabilities. If you require an accommodation to perform the essential functions of your job due to a disability, please contact People Operations at [email protected] to request an accommodation.

This EEO statement reaffirms our commitment to providing a workplace free from discrimination and harassment, in accordance with all applicable laws. We encourage all qualified candidates to apply for employment opportunities at Whip.

Compliance with Laws:

Whip employees are expected to comply with all federal, state, and local laws.

Disclaimer:

This job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of this position.  Essential duties and responsibilities may be added or modified as necessary at any time.