Remote Customer Success Manager — Fleet Growth & Retention

The Descartes Systems Group Inc.; Southwestern Ontario; Remote; CAD 85,000 - 130,000; Full time

Job summary

Descartes Systems Group Inc. is seeking a proactive Fleet Customer Success Manager to drive retention, growth and advocacy across strategic fleet accounts. You will own the post-sale journey, build executive relationships, and ensure Descartes solutions deliver measurable value in efficiency and service.

You will collaborate with Sales, Product and Support to align on outcomes and renewals. Experience with SaaS or enterprise tech, renewals, and data-driven ROI is essential; knowledge of

Qualifications

• Proven success in Customer Success, Account Management or commercially accountable customer-facing roles.
• Experience retaining and growing complex SaaS or enterprise technology accounts.
• Understanding of fleet, logistics, transport or supply chain operations.
• Strong commercial judgement, stakeholder management and executive communication.
• Ability to use customer and operational data to identify risks, demonstrate ROI and drive improvements.
• Experience managing renewals, success plans, escalations and growth opportunities.

Responsibilities

• Customer Retention: Protect recurring revenue through proactive account management, early risk identification and effective renewal planning.
• Customer Value: Develop success plans and demonstrate measurable improvements in fleet efficiency, utilisation, service and costs.
• Product Adoption: Increase solution adoption and executive engagement across strategic accounts.
• Account Growth: Identify and develop qualified expansion opportunities aligned with customer needs and business outcomes.
• Portfolio Management: Within 90 days, segment accounts, establish key relationships and document success plans for priority customers.
• Customer Advocacy: Within 6–12 months, develop customer references, case studies and advocacy opportunities.
• Cross-Functional Collaboration: Align Sales, Product, Support and Professional Services to deliver customer outcomes.

Skills

Customer Success

Account Management

SaaS

Enterprise SaaS

Stakeholder Mgmt

Executive Communication

Renewals & Growth

Data-driven Decisions

Job description

Descartes Systems Group Inc. is seeking a proactive Fleet Customer Success Manager to drive retention, growth and advocacy across strategic fleet accounts. You will own the post-sale journey, build executive relationships, and ensure Descartes solutions deliver measurable value in efficiency and service.

You will collaborate with Sales, Product and Support to align on outcomes and renewals. Experience with SaaS or enterprise tech, renewals, and data-driven ROI is essential; knowledge of