Senior Sales Director - Enterprise

Senior Sales Director

Sales | Enterprise Segment | Full Time | Remote

ENERGY Transportation Group is expanding its enterprise business and is looking for an accomplished logistics seller to help lead that growth. As Senior Director - Enterprise Sales, you will open doors with large shippers, shape solutions around complex transportation needs and turn high-value opportunities into profitable, long-term partnerships.

This is a senior individual-contributor role with real ownership and visibility. You will lead the complete enterprise sales cycle, from targeted prospecting and executive discovery through solution design, negotiation, onboarding and expansion. You will have direct access to executive leadership and the support of Operations, Pricing and Finance to build solutions that work for the customer and for ENERGY.

If you know how to navigate complex buying groups, build credibility with senior decision-makers and close multi-million-dollar logistics opportunities, this role gives you the platform to make a visible impact on ENERGY’s growth.

Key Responsibilities

• Identify and qualify net-new enterprise prospects through outbound prospecting, marketing leads, partner referrals, and executive networks.
• Identify and understand organizational priorities, strategic initiatives, and buying timelines.
• Develop tailored, value-based proposals in collaboration with Operation, that align the company's solutions to each enterprise customer's specific business needs.
• Lead multi-threaded negotiations involving pricing, legal, operations, finance, and executive stakeholders across large organizations.
• Partner with Operations and support teams to ensure a smooth, high-quality new customer onboarding through revenue recognition, establishing a foundation for long-term partnership and retention.
• Conduct structured post-sale reviews to assess customer experience, identify continued growth opportunities, and ensure value realization.
• Work with Operations to identify upsell and cross-sell opportunities by deeply understanding the customer's evolving needs and organizational footprint.
• Maintain strong executive relationships and serve as a trusted strategic advisor to your customers.

What You Bring

• 7+ years of truckload brokerage experience.
• A consistent record of building enterprise pipelines and closing multi-million-dollar revenue opportunities.
• The ability to manage long, complex sales cycles involving executive, operational, procurement, finance and legal stakeholders.
• Executive presence and the confidence to challenge, advise and negotiate with C-suite and VP-level buyers.
• Strong commercial judgment with an understanding of how pricing, service commitments and operational feasibility affect profitability.
• Clear, persuasive written, verbal and presentation skills.
• Strong CRM, forecasting and sales-process discipline.
• A high degree of ownership, resilience and follow-through.

How Success Will Be Measured

• Enterprise new-logo revenue and gross-margin contribution.
• Quality, coverage and conversion of the enterprise pipeline.
• Forecast accuracy and CRM discipline.
• Successful customer launches and early-stage retention.
• Expansion revenue and strength of executive customer relationships.

What We Offer

• Competitive base salary and performance-based incentive structure.
• Comprehensive health, dental and vision benefits.
• A remote role with significant autonomy and direct access to senior leadership.
• A visible opportunity to help shape ENERGY’s enterprise growth strategy.
• Experienced Operations, Pricing and Finance partners who help turn opportunities into executable solutions.
• Professional development and career-growth opportunities in a growing organization.

About ENERGY Transportation Group

At ENERGY, “Driven to be Different” is more than a tagline; it is part of our DNA. We combine Canada-U.S. cross-border expertise, a trusted carrier network, technology-enabled visibility and experienced people who take ownership from start to finish. Our mission is to provide a great work environment where employees can thrive while creating exceptional experiences for our customers and partners.

ENERGY has been recognized through Canada’s Best Managed Companies program, Canada’s Top Growing Companies, Trucking HR Canada’s Top Fleet Employers and Great Place to Work certification.

Our Hiring Commitment

ENERGY Transportation Group is committed to fair, transparent and inclusive hiring practices. We are an equal opportunity employer and consider all qualified applicants without regard to race, colour, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status or any other characteristic protected by applicable law.

We use AI-enabled tools to assist with resume screening and candidate matching based on qualifications and experience. All hiring decisions are made by our People and Culture team. If you require accommodation at any stage of the hiring process, please let us know and we will be pleased to assist.

Your privacy is important to us. Personal information shared during recruitment is used solely for hiring purposes and handled in compliance with applicable data-protection laws.