Director of Operations & Executive Chief of Staff

We are a fast-growing trucking and logistics company operating 16 trucks across two companies and actively scaling. We move freight nationwide and we move fast. There is no bureaucracy here decisions get made, problems get solved, and the right person thrives.

We take care of the people who take care of us. If you are the person this posting describes, you will have a home here for as long as you want one.

The Opportunity

The CEO runs 16 trucks across two companies, a remote international team, active DOT compliance requirements, driver management, and a freight brokerage in development. He needs one exceptional person who owns the back office completely so he can focus on growth.

This is not a traditional assistant role. You run the internal operation. You will know this business as well as the CEO does. You anticipate problems before they surface. You own your domain without being asked twice.

If you need constant direction, this role is not for you.

What You Will Own

- QuickBooks management and weekly financial tracking

- Weekly driver pay and owner operator settlement preparation

- Fuel, toll, and deduction monitoring daily

- Email correspondence and broker communication

- Driver qualification file tracking and compliance document management

- Driver onboarding coordination and follow-up

- ClickUp task management and internal project tracking

- CEO schedule, priorities, and task organization

- Liaison between CEO and remote team

- Hiring support posting, screening, and coordinating interviews

Required Qualifications

- 10+ years of administrative, operations, or executive support experience

- QuickBooks must know it, not just have heard of it

- Exceptional with numbers, detail, and follow-through

- Completes tasks without reminders

- Clear, professional written and verbal communication

- Figures things out independently

Strong Plus

- Trucking, logistics, or transportation industry experience

- Familiarity with DOT compliance or FMCSA requirements

- Direct CEO or business owner support experience

- ClickUp, Airtable, or Google Workspace proficiency

Who We Are Hiring

You have been doing this for years. You are not looking to job-hop, you are looking for the last great role you will need. You are loyal by nature. You take ownership personally. When something falls through the cracks, it bothers you. You do not need to be managed, you need to be trusted. And when you are trusted, you deliver completely.

What We Offer

- Salary range based on experience. Per year, paid bi-weekly

- Direct daily working relationship with the CEO

- Full ownership of your role no micromanagement

- Monday-Friday schedule. Must be able to be on call and respond to calls outside business hours.

- Benefits package in development,compensation reflects this

How To Apply

Send your resume

Include two things in your email:

1. A paragraph describing the most complex operational or administrative challenge you have ever managed and exactly how you handled it.

2. Your answer to this question: "What does loyalty to an employer mean to you?"

Applications without both will not be reviewed. We read every submission personally.

Pay: $50,000.00 - $75,000.00 per year

Application Question(s):

• Describe the most chaotic work environment you have managed and what you did to bring order to it.

Work Location: In person