Lease Purchase Support Specialist

Cowan Systems and Cowan Management•Baltimore, MD

4d•$20 - $24•Onsite

About The Position

The Lease Purchase Support Specialist is responsible for the administration, compliance, and operational support of the Lease Purchase and Independent Contractor Owner Operator (ICOA) programs within the National Road Division. This role serves as the central liaison across Settlements, Maintenance, Claims, Recruiting, Safety, Accounting, and Procurement to ensure seamless execution of agreements, financial processes, and asset lifecycle management. This position plays a critical role in maintaining data integrity, ensuring contract compliance, supporting Independent Contractors, and driving timely, accurate processing of agreements, settlements, and equipment readiness.

Requirements

35+ years of experience in transportation, logistics, fleet operations, or financial/contract administration
Strong understanding of lease purchase or independent contractor models (preferred)
Experience working cross-functionally across operations, finance, and maintenance teams
High attention to detail with strong auditing and analytical capabilities
Proficiency in Microsoft Excel and data management tools
Ability to work in the office 5 days per week
Ability to travel occasionally
Cross-functional collaboration
Financial and contract acumen
Process discipline and compliance
Problem-solving and critical thinking
Communication and stakeholder management
Data accuracy and attention to detail

Nice To Haves

Experience with systems such as Luma , EFS , or similar platforms
Knowledge of trucking industry settlements, escrow structures, and fuel programs
Familiarity with maintenance workflows and third-party vendor management

Responsibilities

Program Administration & Agreements
Administer and manage Independent Contractor Operator Agreements (ICOA) and Lease Purchase Agreements
Process onboarding documentation and agreements through Luma
Execute contract updates, terminations, default notices, demand notices, A/P holds, and 45-day reconciliations
Ensure compliance with all contractual terms, including auditing the Free Lease Week program
Cross-Functional Coordination
Serve as liaison between National Road Division and:
Settlements
Maintenance & FleetRock
Claims / Insurance
Recruiting
Safety
Accounting
Procurement
Respond to inquiries from Independent Contractors and internal stakeholders with accurate and timely information
Escrow, Settlements & Financial Management
Manage and audit maintenance and security escrow accounts
Provide quarterly (or as requested) escrow balance statements to Independent Contractors
Coordinate with Settlements to:
Apply fuel credits or recover fuel expenses
Set up deductions (maintenance, damages, insurance deductibles, etc.)
Ensure proper settlement adjustments for Sub-Truck usage and other chargebacks
Establish and monitor repayment schedules for insurance deductibles (e.g., $250/week)
Identify and escalate accounts with low or negative escrow balances and coordinate recovery plans
Fuel Card & Fraud Management
Manage EFS fuel card assignments and changes
Coordinate with Procurement and Accounting on fuel card setup and updates
Monitor and respond to fraud alerts
Validate transactions with Independent Contractors and reconcile activity within the EFS portal
Equipment Lifecycle & Asset Coordination
Coordinate with Asset Management, Operations, Maintenance, Recruiting, and Accounting to:
Recover leased units
Oversee reconditioning of equipment
Ensure units are lease-ready and properly entered into systems
Ensure all lease details are accurate and updated in a timely manner
Maintenance & Vendor Oversight
Monitor and manage service levels of third-party maintenance providers (e.g., FleetRock)
Ensure Independent Contractors are properly onboarded into maintenance systems and mobile applications
Provide supporting documentation for repairs, invoices, and maintenance activity upon request
Review and validate maintenance invoices for proper GL coding and classification
Claims & Insurance Coordination
Coordinate with Claims and insurance providers to ensure:
Timely reporting of incidents
Proper handling of physical damage claims
Submission of reconditioning claims upon repossession
Track and follow up on all claims through resolution
Coordinate reconciliation with drivers for deductible-related claims
Operational Support & Compliance
Execute Luma documentation for:
Sub-Truck assignments due to downtime
Lease start, transfer, and termination events
Ensure completion of tractor inspections (fuel level, mileage, condition) during:
Lease initiation
Sub-Truck assignment
Unit return (default or end of term)
Reporting, Auditing & Continuous Improvement
Perform routine audits across:
Agreements
Escrow accounts
Settlement deductions
Maintenance and claims activity
Generate reports and provide insights to leadership on program performance
Assess and recommend quarterly adjustments to:
Physical Damage Insurance Rates
Interest Rates
Identify process improvement opportunities and support standardization initiatives