Position Profile
Job Title: Sales & Success Manager
Reports To: President
Location: Remote with Toronto and GTA area preferred

Salary: Base + Commission 

Job Summary:

We are looking for a driven, customer-centric professional to lead our Sales, Marketing, and Customer Success functions for our Dynamic Transport Management Systems (DTMS) platform. This cross-functional role is critical to driving new business, building brand awareness, and ensuring long-term customer satisfaction and retention. The ideal candidate will have a strong understanding of the trucking technology landscape in North America, and a proven ability to manage the full customer journey—from lead generation and onboarding to engagement and renewal.

Key Responsibilities:

Sales & Business Development

• Identify and pursue new sales opportunities in the trucking industry in Canada and USA. 
• Develop and execute strategic sales plans to meet revenue targets.
• Manage the full sales cycle, including lead qualification, product demos, negotiations, and closing deals.
• Maintain and grow a pipeline of prospects through CRM: HubSpot
• Providing weekly and monthly KPI reports for upper management

Customer Success and Account Management

• Serve as the main point of contact for new and existing customers, ensuring successful onboarding and adoption.
• Monitor customer health and satisfaction to drive renewals and reduce churn.
• Proactively identify opportunities for upselling and cross-selling.
• Gather feedback & relay insights to product teams to inform roadmap development.
• Occasional visits to customers in Ontario
  

Marketing

• Design and implement integrated marketing campaigns to increase product visibility
• Work with 3rd party / Corporate team
  • To help develop content marketing including whitepapers, case studies, blogs & webinars.
  • Run GoogleAds and other Pay per click campaigns
• Conduct research to identify trends, customer pain points and competitors activity

Qualifications:

• Bachelor’s degree in Business, Supply Chain, Accounting,  Software or related field
• 5+ years of experience across sales, or customer success roles—preferably in TMS, SaaS, or related trucking B2B software such as ELDs, Loadboards or a WMS
• Strong understanding of Transport Management Systems & related integrated software
• Good understanding of Accounting systems such as Quickbooks, Netsuite or related
• Excellent communication, presentation, and interpersonal skills.
• Experience using CRM and marketing automation tools (HubSpot, Apollo and more)
• Results-oriented, with strong analytical and problem-solving skills.

Preferred Skills & Attributes:

• Experience  in a small team with an independent and entrepreneurial approach
• Ability to balance strategic thinking with hands-on execution.
• Accountability and Goal Driven
• Self starter & Multitasker
• Knowledge of key industry players in North America ( carriers & freight brokers)
• Comfortable with KPIs such as ARR, customer retention rates, close ratios and more
• Knowledge of document management, communications, trucking software, and formal EDI are all assets

**To apply send resume and cover letter to hr@degama.com subject line “Sales Executive”**