Director of Sales

“Here we grow again.” Highlight Motor Group is one of the largest and fastest growing transportation companies in the GTA. As a result of our driven marketing approach and second-to-none work ethic, we are experiencing tremendous growth. To keep up with our growth, we will be seeking experienced, professional, energetic, goal-oriented individuals to complement our organization.

Highlight Motor Group offers an exciting, fast-paced environment that has ideal positions for someone who is looking for a REAL career move. To work for Highlight Motor Group , you must have great people skills, communicate well, have a team-oriented personality, and have the desire to set and achieve goals. As our company is consistently expanding, we are looking for those candidates who are highly motivated and driven by the opportunity for financial reward and career advancement in a family-like working environment.

Job Description:

We are seeking a results-driven Director of Sales to lead, build, and scale the sales function out of our New Jersey terminal. This is a player-coach leadership role responsible for both driving new business directly and recruiting, developing, and managing a high-performing sales team. The Director of Sales will own the terminal’s revenue growth strategy, set the standard for sales execution, and build the team and culture needed to capture mid-size to large accounts across the USA and Canada.

What We Offer:

• Unlimited potential income (Uncapped Commission)
• Above industry average salary, bonus structure, and no pre-defined territories
• Direct access to senior leadership for sales support & career mentorship, defined growth and promotion plan from day 1
• Asset backed logistics company with more than 900 trucks and 2500 trailers on the road across our terminals in Canada and the USA to support your clients 24/7
• Car allowance and other perks
• Company paid benefits package (zero co-pay)

Responsibilities:

• Personally identify and develop new direct B2B opportunities through outbound engagement, networking, and referrals, while leading the team to do the same
• Target and secure mid-size to large accounts requiring over-the-road transportation and warehouse services across USA and Canada.
• Seek, present, and sell end-to-end logistics and 3PL solutions, including LTL, FTL, domestic, cross-border, intermodal, and flatbed services, to drive market growth
• Lead high-value client conversations, conduct needs assessments, and deliver tailored solution proposals
• Develop pricing strategies, proposals, and long-term customer agreements
• Build and maintain a strong, consistent team pipeline and manage opportunities through the full sales cycle (prospecting to closing)
• Maintain accurate pipeline tracking, activity reporting, and timely Hubspot CRM updates across the team
• Support RFP processes, manage quoting and bids, and contribute to SOP development for new and existing clients
• Recruit, hire, onboard, and retain a high-performing sales team for the NJ terminal, scaling headcount in line with growth targets
• Lead, coach, and develop sales representatives through regular one-on-ones, ride-alongs, pipeline reviews, and ongoing skill development
• Set individual and team sales targets, KPIs, and activity standards, and hold the team accountable to them
• Establish and enforce consistent sales processes, cadences, and CRM discipline across the team
• Manage performance end-to-end — recognize and reward top performers, and address underperformance through structured coaching and, where required, formal performance management
• Assign and balance territories, accounts, and leads across the team to maximize coverage and revenue
• Build a culture of performance, accountability, and customer success consistent with HMG’s values
• Forecast team revenue and report pipeline health, wins, and risks to senior leadership
• Partner with HR on workforce planning, compensation structures, and recruitment marketing for the sales function
• Collaborate cross-functionally with operations, pricing, and marketing to enable and support team selling
• Monitor market trends, competitors, and customer needs to identify new opportunities
• Ensure compliance with company policies, procedures, and reporting requirements

Requirements:

• 15+ years of sales experience in logistics, over-the-road LTL & FTL transportation, or 3PL, including 7+ years building and leading sales teams (strongly preferred)
• Proven track record of recruiting, developing, and retaining high-performing sales talent
• Demonstrated success setting targets, managing performance, and driving a team to meet or exceed quota
• Demonstrated success in new business development and outbound sales environments
• Experience with cold outreach, lead generation, pipeline management, and closing deals
• Demonstrated ability to manage the full sales cycle from prospecting to closing
• Cross-border (Canada–US) and/or domestic over-the-road freight experience strongly preferred
• Strong knowledge of the sales process with demonstrated abilities in customer negotiation, communication, and delivering presentations
• Self-motivated leader with a high level of accountability and initiative
• Strong organizational and time-management skills with attention to detail
• Ability to work independently while collaborating effectively with internal teams

Please note that only the candidates selected for the interview will be contacted.