Customer Success Manager – Canadian Customs Experience Required

The Descartes Systems Group Inc.; Southwestern Ontario; Hybrid; CAD 60,000 - 70,000; Full time

Job summary

Descartes Systems Group Inc. is seeking a Customer Success Manager to own renewal strategies and strengthen relationships with a portfolio of approximately 150 mid-market and 10+ multinational accounts across North America.

You will lead QBRs, collaborate with Sales, Product, Support and Professional Services, and drive expansion opportunities while managing renewal risk and customer health.

Qualifications

• 3+ years in Customer Success or strategic account roles.
• Experience in Canadian customs brokerage, freight forwarding, or trade compliance.
• Experience managing customer relationships in a structured environment.
• Experience from operational, customer-facing, sales, or account management roles.

Responsibilities

• Own renewal strategy and lead pricing discussions.
• Lead quarterly business reviews (QBRs) focused on value realization and long-term partnership.
• Identify cross-sell and upsell opportunities with customer workflows and adoption patterns.
• Maintain disciplined account management processes, CRM hygiene, and renewal timelines.
• Partner with Sales and cross-functional teams to support expansion strategy.

Skills

Communication skills

Commercial curiosity

Account planning

Organizational skills

Cross-functional teamwork

Problem solving

Job description

Descartes Unites the People and Technology that Move the World

The need for efficient, secure, and agile supply chains and logistics operations has become ever more critical and complex. By combining innovative technology, powerful trade intelligence and the reach of our network, Descartes helps get goods, information, transportation assets, and people where they’re needed, when they’re needed. We’re one of the most broadly deployed logistics and supply chain technology companies in the world. More than 26,000 customers around the globe use our cloud-based solutions to transform the way they move inventory and information to enhance productivity, better serve customers, thrive competitively, keep pace with evolving regulations, and respond to rapidly changing market conditions. Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what’s most important to them. Learn more at www.descartes.com.

We’re growing fast and invite you to join our amazing team.

To own the strategic and commercial management of a growing Canadian customs brokerage customer portfolio, supporting customer retention, structured account growth, and long-term customer success. The Customer Success Manager is commercially accountable for protecting and expanding revenue within an assigned book of approximately 150 customers while proactively strengthening customer relationships and identifying growth opportunities.

This role operates in a forward-looking, disciplined manner balancing renewal leadership, customer engagement, and expansion development and sits at the intersection of customer success, commercial account management, and logisticstechnology consulting. Customers range from mid-market customs brokers to large multinational logisticsproviders operating complex import/export and compliance environments across North America.

Why This Role Matters

This is a highly visible role supporting some of Descartes’ most strategic Canadian customs brokerage and logisticscustomers during a period of significant market change and growth. The successful candidate will work cross-functionally with Sales, Product, Support, Professional Services, and leadership teams while gaining deep exposure to customs brokerage operations, trade compliance, and logisticstechnology. This role is ideal for someone early in their career who is ambitious, commercially curious, and looking to grow into broader leadership, commercial, product, or customer-facing opportunities over time.

What Success Looks Like in the first 12-18 Months

An A-Player in this role consistently delivers the following results:

Revenue Protection & Retention

• Maintain strong renewal performance through proactive engagement and risk mitigation
• Develop and execute structured retention plans for identified yellow/red accounts before renewal impact

Customer Engagement & Partnership

• Conduct formal Quarterly Business Reviews (QBRs) focused on value realization, operational alignment, and long-term partnership
• Improve responsiveness, customer sentiment, and stakeholder engagement across the portfolio
• Build trusted relationships with operational users, managers, and executive stakeholders

Expansion & Growth

• Generate qualified expansion opportunities aligned to documented customer objectives and business priorities
• Identify opportunities for broader adoption of Descartes solutions and services
• Partner closely with Sales on structured cross-sell and upsell motions

Portfolio Management

• Manage approximately 150 mid-market accounts and 10+ multinational enterprise accounts
• Prioritize activity based on renewal timing, customer health, growth potential, and operational risk
• Maintain disciplined CRM hygiene and structured account planning

Core Responsibilities

Strategic Customer Management

• Own renewal strategy and lead pricing discussions aligned to customer value realization and long-term partnership
• Develop structured account plans tied to retention, adoption, and growth
• Lead customer conversations focused on operational improvement, product adoption, and strategic partnership

Customer Engagement & QBR Leadership

• Lead strategic QBRs and customer reviews that elevate discussions beyond support tickets and tactical updates
• Proactively uncover customer goals, risks, and growth opportunities through thoughtful discovery
• Engage stakeholders ranging from day-to-day operators through executive leadership

Growth & Expansion

• Identify cross-sell and upsell opportunities based on customer workflows, adoption patterns, and operational priorities
• Create and document qualified opportunities in CRM with clear business drivers and stakeholder alignment
• Partner with Sales to support expansion strategy and smooth commercial handoffs

Risk Management

• Monitor portfolio health and proactively identify churn or renewal risks
• Execute measurable mitigation plans before commercial impact occurs
• Escalate customer concerns early and coordinate internal resources effectively

Cross-Functional Collaboration

• Partner with Sales, Product, Support, Professional Services, and leadership teams to coordinate customer strategy
• Advocate internally for customer priorities while balancing operational and commercial realities
• Help customers navigate organizational change, product enhancements, and evolving regulatory requirements

Operational Excellence

• Maintain disciplined account management processes, CRM updates, renewal timelines, and customer documentation
• Proactively guide customers toward operational best practices and long-term value realization rather than operating in a reactive support-only capacity

Experience & Aptitudes

Required Experience

• 3+ years in Customer Success, Strategic Account Management, logistics operations, trade compliance, or similar customer-facing commercial roles
• Practical experience within Canadian customs brokerage, freight forwarding, or trade compliance environments is required
• Experience may come from operational, customer-facing, sales, or account management backgrounds
• Experience managing customer relationships, renewals, or operational accounts in a structured environment

Industry Knowledge

• CSA
• CHB Finance
• CARM
• Tariff classification
• Duty remediation
• Sufferance operations
• Trade programs
• Export / trade compliance workflows

Skills & Attributes

• Strong written and verbal communication skills, with confidence interacting directly with operational stakeholders, managers, and customer leadership teams
• Commercial curiosity and strong problem-solving ability
• Ability to build structured account plans tied to retention and growth
• Strong organizational skills and disciplined execution
• Comfortable navigating ambiguity and cross-functional environments
• Coachable, collaborative, and motivated to continuously improve
• We’re looking for someone who is proactive, intellectually curious, organized, and energized by solving operational and customer challenges in a fast-moving environment
• Interest in developing broader commercial, leadership, or strategic account management capabilities over time
• This role is focused on proactive customer engagement and strategic account management — not reactive ticket-based support

Culture Add (Our TEAM Values)

• Transparency –Open, honest communication that builds trust.
• Excellence &Expertise– High standards and continuous mastery of your craft.
• Accountability –Ownership of outcomes and commitment.
• Metric-Driven Results– Data-informed decisions focused on measurable impact.

Salary Range:

$60,000 – $70,000 CAD annually plus 20% Commission-Compensation information provided is a good faith estimate for this position only. Factors that may be used to determine your actual salary may include your specific skills as well as the years of experience you have. Similar positions located in different geographic regions will not necessarily receive the same compensation.

Join Us

As we scale, we’re looking for new doers, collaborators and innovators to join Descartes in uniting the people and technology that move the world as the Global Leader in Logistics and Supply Chain Technology. We’re entrepreneurial, hardworking, geeky-in-a-good way problem solvers. Guided by our values, we nurture a TEAM focused culture that invests in people and creates opportunities for advancement across a broad spectrum of career paths. We prioritize work-life balance and foster an environment with the space to take ownership, to be heard, and to carve a path for your individual accomplishments to help drive our success.

Descartes also has a deep sense of environmental responsibility. Learn more about how we helped our customers save over 552,000 metric tons of CO2 in 2020 by reducing fuel and paper consumption: https://www.descartes.com/who-we-are