$215,000–$250,000 Base Salary | 20% Annual Performance Bonus
Full-Time | Remote, United States | No AI or Coding Experience Required
Upgrade Minds is hiring a senior trucking operations leader who understands the real problems inside asset-based trucking companies.
We need someone who can identify costly pain points, repetitive tasks, communication gaps, and broken workflows across trucking operations. You will then work directly with our AI developers and automation engineers to turn those problems into practical solutions.
You do not need previous AI experience.
We are hiring you because you understand trucking. We will provide the AI and automation training.
About Upgrade Minds
Upgrade Minds builds AI and automation solutions for trucking and transportation companies.
We help carriers reduce repetitive office work, answer calls faster, improve communication, connect their existing systems, and give employees more time to focus on important decisions.
Our solutions may include AI voice agents, workflow automation, document processing, system integrations, automated follow-up, and operational reporting.
We are especially focused on helping asset-based trucking companies with approximately 100–2000 trucks.
What You Will Do
You will act as the bridge between trucking companies and our technical development team.
Your main responsibility will be to uncover real operational pain points and help Upgrade Minds build solutions that trucking companies will use and pay for.
You will:
- Interview trucking owners, executives, dispatchers, safety teams, billing teams, drivers, and other employees.
- Identify repetitive tasks that waste time or create unnecessary costs.
- Find areas where calls, emails, text messages, documents, and follow-ups are being missed.
- Review how work moves through dispatch, after-hours operations, customer service, safety, compliance, billing, maintenance, recruiting, and administration.
- Discover where employees repeatedly copy information between systems.
- Map current workflows from beginning to end.
- Measure how often problems happen and how much time or money they cost.
- Rank automation opportunities based on value, risk, and difficulty.
- Explain trucking workflows to AI developers and automation engineers.
- Turn operational problems into clear requirements that developers can build.
- Review and test automation using realistic trucking situations.
- Define when an automated system should stop and transfer the situation to a person.
- Help Upgrade Minds create repeatable solutions for multiple trucking clients.
- Join selected client discovery calls, planning sessions, and developer meetings.
- Help shape Upgrade Minds’ trucking products, services, and long-term industry strategy.
Pain Points You May Help Solve
You may help Upgrade Minds find and solve problems involving:
- Repetitive dispatch calls
- After-hours driver calls
- Missed calls and slow response times
- Driver check calls and status updates
- Customer and broker tracking requests
- Breakdown and delay intake
- Pickup and delivery appointment information
- Driver communication by phone, text, and email
- Repetitive data entry
- Load-status updates
- Missing proof-of-delivery documents
- Rate confirmation processing
- Bill of lading processing
- Detention and accessorial documentation
- Delayed invoicing
- Driver onboarding
- Safety and compliance reminders
- Maintenance requests
- Customer follow-up
- New lead qualification
- Internal reporting
- Information moving between disconnected systems
The goal is not to automate everything.
The goal is to automate repetitive work while keeping people involved in situations that require judgment, safety decisions, negotiation, or personal attention.
Voice Automation Opportunities
You will help our team determine how AI voice agents could support calls during and after business hours.
Examples may include:
- Answering basic driver questions
- Collecting load and location details
- Handling routine status requests
- Gathering information about delays or breakdowns
- Sending call summaries to dispatchers
- Routing urgent calls to the correct person
- Answering common customer questions
- Collecting new customer or driver information
- Scheduling calls or appointments
- Following up for missing documents
You will help define:
- What questions the AI should ask
- What information it may provide
- Which system it should check
- What information it should record
- When it must transfer the call
- Which situations should always be handled by a person
Systems and Integrations
You will help our developers understand how trucking companies use systems such as:
- Transportation Management Systems
- Electronic Logging Devices
- Telematics platforms
- Dispatch software
- Fleet-management platforms
- Customer relationship management systems
- Phone and call-center systems
- Email and text-message platforms
- Accounting and billing systems
- Document-management systems
- Fleet-maintenance software
You do not need to program or build these integrations.
You should understand how the systems are used, which information should move between them, and what a successful solution should accomplish.
Who We Are Looking For
You may be a strong fit if you have worked as a:
- Chief Operating Officer
- Vice President of Operations
- Director of Operations
- Director of Fleet Operations
- Transportation Operations Director
- Fleet Director
- General Manager
- Terminal Manager
- Senior Operations Manager
- Senior Dispatch Leader
- Trucking Operations Consultant
We are looking for someone who understands how multiple trucking departments work together—not someone who only knows one small part of the operation.
Required Experience
- At least 10 years of trucking or transportation industry experience
- At least five years in an operations leadership position
- Direct experience working inside an asset-based trucking company
- Strong knowledge of dispatch and after-hours operations
- Experience with driver communication, load management, or customer service
- Familiarity with billing, safety, compliance, maintenance, or back-office operations
- Experience using TMS, ELD, telematics, dispatch, or fleet-management systems
- Ability to identify the root cause of an operational problem
- Ability to explain a trucking workflow clearly from beginning to end
- Strong communication and listening skills
- Ability to work with company owners, employees, and technical developers
- Willingness to learn AI and automation concepts
Equivalent senior-level trucking experience will also be considered.
AI Experience Is Not Required
Previous experience with AI, automation, coding, or software development is not required.
Upgrade Minds will provide training on:
- What AI can and cannot do
- How AI voice agents work
- How business processes are automated
- How to document requirements for developers
- How to review workflow diagrams
- How to test an automated system
- How to create human-escalation rules
- How to work effectively with AI developers and automation engineers
We need your trucking knowledge, practical judgment, and ability to uncover important problems.
What Success Looks Like
During your first year, success may include:
- Building a detailed library of trucking industry pain points
- Identifying the highest-value automation opportunities
- Helping clients clearly understand where they are losing time or money
- Creating workflow maps developers can use
- Helping launch practical AI voice and workflow automation solutions
- Testing solutions before they are used in live operations
- Reducing missed calls, manual work, delays, and data-entry errors
- Helping trucking companies improve response times and customer service
- Creating repeatable solutions Upgrade Minds can offer to future clients
- Becoming a trusted industry leader within Upgrade Minds
Compensation
- Base salary: $215,000–$250,000 per year
- Annual performance bonus: 20% target bonus, separate from base salary
- Employment type: Full-time
- Workplace: Remote within the United States
Base salary will depend on trucking leadership experience, operational knowledge, communication skills, systems experience, and overall fit.
The performance bonus will be based on agreed individual and company goals and is paid separately from base salary.
How to Apply
Please submit your résumé or LinkedIn profile.
In your application, briefly answer:
- What trucking leadership roles have you held?
- What size fleets have you managed or supported?
- Which TMS, ELD, telematics, dispatch, or fleet-management systems have you used?
- What are five repetitive tasks inside trucking companies that should be improved or automated?
- Describe one operational pain point you helped solve and the result.
Final Message
You have spent years seeing where trucking operations lose time, money, and valuable employees.
Now you can use that experience to help build better solutions for the industry.
- You bring the trucking knowledge. Upgrade Minds will provide the AI training and development team