Customer Success Manager

The Descartes•Waterloo, ON

31d•$65,000 - $75,000•Remote

About The Position

This role is responsible for the strategic and commercial management of a growing Canadian customs brokerage customer portfolio. The primary goals are to support 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 position operates in a forward-looking, disciplined manner, balancing renewal leadership, customer engagement, and expansion development. It sits at the intersection of customer success, commercial account management, and logistics technology consulting. Customers range from mid-market customs brokers to large multinational logistics providers operating complex import/export and compliance environments across North America. This is a highly visible role supporting some of Descartes’ most strategic Canadian customs brokerage and logistics customers 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, gaining deep exposure to customs brokerage operations, trade compliance, and logistics technology. 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.

Requirements

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.
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.
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.

Nice To Haves

Specific knowledge of the following is considered a strong asset: CSA, CHB Finance, CARM, Tariff classification, Duty remediation, Sufferance operations, Trade programs, Export / trade compliance workflows.

Responsibilities

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.
Protect and expand revenue within an assigned book of approximately 150 customers while proactively strengthening customer relationships and identifying growth opportunities.
Maintain strong renewal performance through proactive engagement and risk mitigation.
Develop and execute structured retention plans for identified yellow/red accounts before renewal impact.
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.
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.
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.
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.
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.
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.
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.
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.
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.