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Sr Transportation Manager

May 30, 2026

About the Job Location: Sterling, VA Schedule: Monday–Friday with rotating Saturdays The Senior Transportation Manager is responsible for the leadership, development, and day-to-day management of frontline transportation employees. This role directly oversees a team of 15–20 drivers and helpers, with full ownership of onboarding, training, coaching, mentoring, and performance management. This is a highly visible, field-based position that spends the majority of time working directly with frontline staff to ensure safe, efficient, and reliable route execution. The Senior Transportation Manager builds strong employee relationships, reinforces a culture of accountability and safety, and drives engagement and performance across the team. The role focuses on maintaining service excellence, ensuring compliance with company policies and regulatory requirements, and identifying opportunities to improve route productivity and operational efficiency. This position manages drivers and helpers exclusively, with no direct reports at the management level. The ideal candidate is a hands-on, people-first leader with strong transportation or logistics experience, a passion for developing teams, and the ability to thrive in a fast-paced, operational environment. What You'll be Doing - Onboarding - New Route Managers - Ensuring new frontline employees have tools, instruction, and feedback for successful daily duties - Meet with new frontline employees daily to ensure consistent communication and support of onboarding - Developing - Provide timely and consistent touchpoints with frontline employees. - Regular review of best practices to enhance daily performance - Focus on understanding and progress of frontline employee career goals - Coaching - Identify and address improvement opportunities and collaborate with frontline employees to ensure continued success - Actively practice and seek feedback on coaching conversations. - Mentoring- Lead by example to ensure safety practices are paramount with each employee - Teaching and developing an understanding of the WM Way - Performance Management - Conducts Root Cause Investigations for all injuries and incidents, ensuring consistent discipline and retraining. - Documents and maintains records required by regulatory agencies such as the Department of Transportation. - Reviews and audits documentation related to route operations on a daily basis (e.g., DVIRs, driver time and attendance, open tickets), following up where appropriate. - Visits customers and customer sites to evaluate and resolve safety issues, seeking service alternatives where appropriate. What does it take to be a Sr Transportation Manager with WM? A. Required Qualifications - Associate's Degree (accredited) or in lieu of degree, - High School Diploma or GED (accredited) and two (2) years of relevant work experience. - 2 years of relevant work experience (in addition to education requirement) - Must be at least 18 years of age - Legally eligible to work in the country where the position is located - Valid Driver's License B. Preferred Qualifications Physical Requirements Listed below are key points regarding physical demands, physical and occupational risks, and the work environment of the job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions of the job.☒ Combination: This job operates in a mix between an office environment and plant/field environment and routinely requires the use of standard office equipment such as computers, phones, copy machines, etc. About our Benefits At WM, each eligible employee receives a competitive total compensation package including Medical, Dental, Vision, Life Insurance and Short Term Disability. As well as a Stock Purchase Plan, Company match on 401K, and more! Our employees also receive Paid Vacation, Holidays, and Personal Days. Please note that benefits may vary by site. If this sounds like the opportunity that you have been looking for, please click Apply.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...