Claims and Operations Specialist (Total Loss)

This is a remote position.

DriveWhip is a mobility provider in the DC area, with offices in multiple cities, including Boston; we lease/rent vehicles to Uber, Lyft and other On-Demand or Rideshare drivers. 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

Whip is seeking an organized, driven Claims and Operations Specialist to own the settlement of total loss claims across our rental fleet. Once a vehicle has been identified as a likely total loss, this role manages every step of the settlement through final payment.

This is an operations-heavy role. Beyond settling the claim itself, you will be the central point of contact between Claims, Finance, Compliance, Transportation, and our vendor partners, including body shops. You will work directly with body shops throughout the vehicle inspection process and vehicle pick-up, keeping every party informed and making sure nothing stalls between inspection, valuation, settlement, vehicle movement, and payment.

The ideal candidate is highly organized, persistent in follow-up, comfortable negotiating settlements, and able to balance many open settlements at once without letting any of them slip.

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

Total Loss Settlement

• Take ownership of total loss claims once liability is confirmed and the vehicle is identified as a probable total loss.
• Review vehicle valuations (e.g., CCC) for accuracy and calculate settlement figures, including actual cash value, taxes, fees, salvage, and any applicable deductions.
• Negotiate and finalize total loss settlements with carriers, claimants, and other parties within assigned authority, pushing back on low or unsupported valuations and driving settlements to timely resolution.
• Coordinate title, lienholder, and release documentation required to complete the settlement.

Cross-Team & Vendor Coordination

• Serve as the single point of contact for total loss status across internal teams, keeping everyone aligned as each claim progresses.
• Report settlement status, amounts, and outcomes to the Finance team for accruals, payments, and reconciliation.
• Provide required information and documentation to the Compliance team, including title, registration, and regulatory reporting needs.
• Coordinate with the Transportation team on vehicle location, storage, release, and transfer to salvage or auction.
• Work directly with vendors, including body shops, throughout the vehicle inspection and pick-up process, obtaining inspection findings and documentation, and confirming release and any outstanding storage or teardown charges.

Payment Follow-Up & Recovery

• Track every open settlement through to payment received.
• Follow up aggressively and consistently with carriers, adjusters, and other parties on outstanding payments, escalating stalled settlements and identifying what is needed to move them forward.
• Confirm receipt of funds and ensure payments are properly logged and reconciled with Finance.

File Management & Communication

• Maintain clear, complete, and accurate notes and documentation in every claim file and internal tracker.
• Manage a high volume of concurrent total loss settlements, prioritizing by age, value, and urgency.
• Communicate professionally and proactively with carriers, claimants, vendors, and internal stakeholders.
• Identify recurring bottlenecks in the total loss process and contribute to improving workflows and tracking.

Qualifications Required:

• 2+ years of experience in an operations, administrative, or coordination role, ideally in insurance, fleet, rental, or transportation.
• Highly organized, with a proven ability to manage a large volume of open items accurately and follow up persistently with external parties to get answers and payments.
• Ability to communicate clearly with multiple teams (Finance, Compliance, Transportation) and keep them aligned.
• Comfort negotiating and holding a position when presenting settlement figures.
• Proficiency with Google Workspace or Microsoft Office, particularly spreadsheets.

Preferred Required:

• Claims experience, specifically first-party comprehensive/collision or third-party property damage claims.
• Direct experience settling total loss claims, including valuations, salvage, title, and lienholder payoffs.
• Familiarity with claims management and valuation platforms such as CCC and Snapsheet.
• Exposure to working with rental, rideshare, or commercial fleet operations.
• Experience working in startup or fast-paced environments, with the ability to wear multiple hats and adapt to evolving priorities.

Salary: $10 - $15 hourly (depending on experience)

What We're Looking For

We're looking for an organized, tenacious operator who takes ownership of every settlement from transfer to payment. The right person doesn't wait for answers. They chase them, keep a clear view of where every file stands, and make sure no settlement or payment falls through the cracks.

The successful candidate will be comfortable negotiating settlements, holding firm on supported figures, and working across Claims, Finance, Compliance, and Transportation to keep vehicles and dollars moving.

This is an opportunity to play a key role in building Whip's total loss process and helping create a more efficient, disciplined, and scalable claims organization.