Administrative Operations Specialist – Parking Ticket & Toll Cleanup

We are a small vehicle rental company in the Boston, Massachusetts area looking for a highly organized freelancer to help us clean up historical parking tickets, municipal citations, and older toll records associated with our rental vehicles.

This is a short-term administrative research and cleanup project, with the possibility of limited ongoing work afterward.

We expect the initial cleanup project to take roughly 15–20 hours, more or less, depending on the number of outstanding citations and the amount of follow-up required with individual municipalities.

*Scope of Work*
Parking Tickets & Municipal Citations

You will:

- Review parking tickets and citation notices that have already been scanned into our virtual mailbox.
- Enter all tickets into a tracking spreadsheet that we will provide.
- Search municipal websites and contact municipalities to identify additional outstanding citations that we may not have received or retained.
- Contact municipalities by phone and/or email when necessary.
- Follow a provided script and process when communicating with municipalities.
- Determine the current status of older citations, including citations that may already be 30+ days old.
- Document any deadlines, forms, supporting documents, or next steps required by each municipality.
- Flag anything unclear or unusual for owner review rather than making assumptions.

Municipalities may include Boston, Cambridge, Somerville, Newton, Revere, Lynn, Framingham, Worcester, Brockton, Milton, Plymouth-area municipalities, and other Massachusetts cities or towns identified during the project.

*Matching Tickets to Renters*

Our historical rental dates and vehicle assignments are already maintained in our rental management system.

You will:

- Determine who had possession of the vehicle on the date of each citation.
- Match citations to the appropriate renter and rental agreement.
- Review vehicle assignment history when renters changed vehicles during a rental period.
- Identify any missing or unclear information and flag it for review.

You will not be expected to reconstruct our rental history from scratch.

*Preparing Documentation*

Depending on the requirements of each municipality, you may need to:

- Gather the applicable rental agreement.
- Gather renter driver's-license information provided by us.
- Organize supporting rental documentation.
- Prepare company letters using templates we provide.
- Complete or prepare municipality forms.
- Prepare print-ready packages when documents must be physically mailed.
- Prepare electronic submissions when applicable.
- Maintain clear records showing what has been completed and what still requires follow-up.

Initially, submissions will be reviewed before anything is formally sent or filed.

*Historical Toll Cleanup*

You may also assist with older toll records by:

- Reviewing approximately the prior 12–18 months of historical toll information.
- Matching tolls to the renter who had possession of the vehicle at the time.
- Identifying tolls that were already billed or resolved.
- Identifying unresolved tolls requiring further action.
- Updating the tracking spreadsheet with the status and required next steps.

*Tools & Systems*

We will provide access to the systems and information needed for the project.

Tools may include:

Google Sheets
RentSys rental management software
Anytime Mailbox
Scanned rental agreements and citation notices
Supporting customer and vehicle records

Prior experience with RentSys or Anytime Mailbox is not required. These systems are straightforward and we can provide guidance.

Strong experience using Google Sheets or Excel is required.

..... What We Are Looking For. ...........

We are looking for someone who is:

- Highly organized and detail-oriented
- Strong at online research
- Comfortable making professional phone calls
- Comfortable contacting government offices and municipalities
- Able to follow scripts and established procedures
- Careful with dates and documentation
- Able to work independently
- Good at keeping accurate notes and status updates
- Able to recognize when something needs to be escalated rather than guessing
- Reliable with follow-up

Experience with administrative case management, government paperwork, insurance claims, fleet administration, legal support, compliance, collections, or similar work is helpful but not required.

Potential Ongoing Work

The initial project is focused on bringing our historical ticket and toll records current.

For the right person, there may be an opportunity for limited ongoing work afterward, such as periodically checking municipalities for new outstanding citations and processing routine ticket-related administrative work.

This ongoing work would likely require only a small number of hours periodically.