Demo

Settlements Specialist

Heniff Transportation Systems
Oak Brook, IL Full Time
POSTED ON 4/11/2026
AVAILABLE BEFORE 5/10/2026

Position Summary

The Settlements Specialist is responsible for ensuring all driver and carrier pay is calculated accurately and timely across the Heniff family of companies. This person is critical for ensuring a smooth weekly pay process for all of our Company and Owner Operator drivers.


Duties and Responsibilities:

  • Process Company and Owner Operator driver's settlements using the transportation management system (TMW) application.
  • Identify, escalate (when necessary), and resolve disputed issues with driver or carrier pay
  • Audit deductions for items such as fuel, escrows, insurance, and lease payments.
  • Collaborate with cross functional teams to ensure all urgent driver pay related issues are resolved on a timely basis ensuring that drivers have a positive experience
  • Prepare Settlement and other reports as requested.
  • Adhere to internal accounting controls to ensure financial compliance
  • Perform additional duties as required.


Education and Experience:

  • Bachelor's degree or equivalent work experience
  • Proficiency with Microsoft Suite applications including Word, Outlook and Excel
  • 1 years of related experience


Preferred Qualifications:

  • Experience using the TMW (transportation management system)
  • Prior experience in driver settlements pay


Essential Qualifications:  

  • Strong organizational and analytical skills
  • Critical thinking skills
  • Solid communication skills and attention to detail
  • Ability to work effectively with all levels of the organization
  • Strong customer service orientation, ensuring needs and deadlines are met in a timely manner
  • Demonstrate a positive, proactive and motivated attitude
  • Proven focus on continuous improvement in the workplace
  • Ability to adapt to change in a fast-paced organization
  • Proven problem solver, anticipates challenges and is both responsive and resourceful


Language Skills

  • Ability to read, write and speak English proficiently


Physical Demands: 

  • While performing the duties of this job, the employee is regularly required to stand, sit, talk, hear, reach, and use hands and fingers to operate a computer, telephone, keyboard, mouse and Touch screen.
  • Ability to operate in a constant state of alertness and safe manner.


Work Environment: 

  • The position typically operates in a standard office environment.
  • This position routinely uses office equipment such as computers and phones.


Benefits Package:

  • Medical, Dental, Vision, Life, and Disability Insurance
  • 401(k) Plan Company Match
  • Paid Time Off (120 hours yearly)
  • Company Paid Holidays
  • Paccar Online Training Provided


Salary Range:

Disclaimer:  The salary range for this position is $22.00 - $26.50 hourly. This range is based on market data and internal equity. The final offer will be determined by various factors, including the candidates experience, education, skills, qualifications, and geographic location.


The Heniff Family of Companies, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Heniff treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes and general treatment during employment, including on the basis of actual or perceived race, creed, color, religion, sex, age, sexual orientation, gender identity and/or expression, alienage or national origin, ancestry, citizenship status, marital status, veteran status, or disability.

Salary : $22 - $27

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