A privately owned transportation technology business is seeking an experienced, hands-on President & CEO to lead its operations, build its team, and drive its development and growth.

We are developing a digital freight platform that connects shippers directly with carriers and owner-operators. Our goal is to combine practical transportation expertise, strong industry relationships, and effective technology to create a service that members trust and use regularly.

We need a leader who understands transportation from the ground up—someone who knows dispatch, respects the realities of operating a truck, can earn the confidence of owner-operators, and has the business judgment to turn an chance into a well-managed operation.

This is not simply a senior dispatch position. It is an opportunity to take responsibility for building and running a business.

The opportunity

Reporting directly to the founder, you will lead the company’s day-to-day management, operational execution, team development, and commercial performance.

The founder remains involved in strategy and major business decisions. Your responsibility will be to translate that direction into action, make decisions within the approved plan and budget, and establish an operation that does not depend on the founder’s daily involvement.

This position is suited to an accomplished transportation general manager, operations executive, or entrepreneurial leader who is ready for broader responsibility. A previous President or CEO title is not required; demonstrated leadership and results are.

What you will lead

Business operations and financial performance
Develop and execute the operating plan, manage budgets, establish priorities, and provide clear reporting on revenue, expenses, customer activity, and business performance. Identify problems early and bring forward practical solutions.

Carrier and owner-operator relationships
Build and maintain a reliable, engaged network of carriers and owner-operators. Lead recruitment, onboarding, communication, retention, and dispute resolution. Establish a reputation for fairness, responsiveness, and follow-through.

Shipper relationships and commercial growth
Develop shipper relationships and repeat freight opportunities that create real value for participating carriers.



Grow subscription revenue and member retention while maintaining disciplined spending and service standards.

Dispatch-informed processes and technology delivery
Apply your transportation experience to improve load posting, bidding, booking, tracking, documentation, and support workflows. Work with technology partners to prioritize improvements, test functionality, and ensure the platform meets practical operational needs. Preserve the direct shipper-to-carrier model rather than treating the business as a conventional dispatch office.

People, accountability, and service quality
Recruit, train, and lead the team. Establish clear responsibilities, performance expectations, operating procedures, and escalation processes. Build a culture in which customers receive dependable support and employees understand what they are accountable for.

The experience we are looking for

- Substantial transportation and logistics experience, ideally including 10 or more years in the industry and at least five years leading teams or operations.
- Strong hands-on dispatch and transportation management knowledge, including freight coordination, equipment requirements, scheduling, service exceptions, and carrier communication.
- Proven owner-operator and carrier relationship management, with direct experience recruiting, onboarding, retaining, and resolving issues with independent operators and small fleets.
- Demonstrated business management ability, including budgeting, financial reporting, customer development, staff leadership, and responsibility for measurable operating results.
- Confidence working with transportation technology, including dispatch systems, transportation management systems, load boards, or related platforms. You must be able to communicate operational requirements clearly and hold suppliers accountable; software-development experience is not required.

Experience building an operation, introducing new services, implementing systems,



or working in an early-stage business would be particularly valuable.

The person who will succeed here

You are comfortable speaking with an owner-operator, resolving a difficult customer issue, reviewing a budget, and leading a management meeting.

You are commercially minded without losing sight of the people delivering the service. You understand that strong relationships require honest communication, consistent standards, and commitments that are followed through.

You can work independently, make sound decisions with incomplete information, and recognize when an issue requires escalation. You are willing to be hands-on while building the people and processes needed to delegate effectively.

Most importantly, you are looking for responsibility and the opportunity to build something—not simply a more senior title.

Compensation, benefits, and perks

We are offering a compensation package designed to recognize both leadership responsibility and measurable results:

- $135,000–$155,000 CAD annual base salary, depending on experience and qualifications.
- Generous performance and year-end bonuses, tied to agreed individual and company results, including business growth, member retention, operational execution, and financial performance.
- A full employee benefits package.
- Four weeks of paid vacation annually.
- A company-provided 407 ETR transponder.

You will also have direct access to the founder, meaningful decision-making authority within the approved business plan, and the opportunity to recruit and develop your team.

What success will look like

During your first months, you will establish a clear operating plan, assess platform and service readiness, strengthen shipper and carrier relationships, and put reliable reporting and support processes in place.

As the business develops, success will be measured by an engaged member base, recurring revenue, repeat platform use, effective cost management, and a team capable of delivering dependable service without constant founder intervention.

Pay: $115,000.00-$125,000.00 per year

Benefits:

- Casual dress
- Commuter benefits
- Company car
- Company events
- Dental care
- On-site parking
- Paid time off
- Tuition reimbursement

Work Location: In person

📌 President — Transportation & Logistics Technology (Etobicoke)
🏢 Important Business
📍 Etobicoke