Role Type: Full-Time Work Location: Remote (Toronto, Canada)

Reports to: Head of Customer Success

Work Authorization: Candidates must have legal authorization to work in Canada at the time of hire. CWILL is not able to provide visa sponsorship at this time.

The Role

CWILL is hiring a Customer Success Manager for TrackingMore - our multi-carrier parcel tracking API platform used by eCommerce merchants, logistics platforms, and developers worldwide. www.trackingmore.com

You will own the post-sales relationship with our API customers - helping technical merchants and platform integrators get up and running, driving deeper product adoption, and ensuring they're getting real business value from the integration. This is a hands-on, customer-facing role that sits at the intersection of customer success, light technical support, and product feedback.

The ideal candidate is customer-obsessed, comfortable discussing API workflows and webhook configurations with a developer, and equally at ease talking logistics KPIs with a merchant ops team. You don't need to be an engineer, but you need to be technically curious, resourceful, and genuinely invested in customer outcomes.

What You'll Do

Onboarding & Integration Adoption

• Guide new customers through API onboarding - including API key setup, endpoint configuration, carrier mapping, and webhook integration.
• Work with merchants and their dev teams to ensure TrackingMore is correctly integrated into their order management or post-purchase workflows.
• Identify integration gaps or early adoption risks and proactively help customers reach their first successful tracking milestone.
• Maintain onboarding documentation, integration checklists, and enablement materials for common customer segments (Shopify merchants, 3PLs, logistics platforms).

Account Management & Retention

• Manage a portfolio of SMB and mid-market API customers as their main point of contact.
• Monitor account health signals: API call volume trends, carrier success rates, error rates, and renewal or churn indicators.
• Run regular customer check-ins focused on tracking performance, carrier coverage needs, and business outcomes.
• Surface upsell, cross-sell, and renewal opportunities - including plan upgrades, carrier add-ons, and expanded API usage.

Support & Issue Resolution

• Triage customer issues related to API performance, carrier data delays, webhook failures, or tracking accuracy - coordinating with engineering and carrier ops through to resolution.
• Identify recurring support themes (missing carriers, parsing errors, data latency) and route them as structured product feedback.
• Maintain high standards for responsiveness, technical accuracy, and follow-through.

Insights & Collaboration

• Capture customer feedback, carrier coverage gaps, and competitive insights from daily merchant and developer conversations.
• Share customer context with Product and Engineering to inform carrier roadmap, API feature priorities, and documentation improvements.
• Keep CRM records, integration notes, and account health data accurate and up to date.

Requirements
What We're Looking For

• Bachelor's degree or equivalent practical experience.

• 2-4 years in Customer Success, Account Management, or Technical Support - ideally at a SaaS or API-first company

• Comfortable reading API documentation and troubleshooting basic integration issues (you don't need to write code, but you should know what a webhook is)

• Experience working with eCommerce, logistics, or shipping technology is a strong plus

• Clear written and verbal communicator - able to translate technical issues for non-technical stakeholders and vice versa

• Self-starter comfortable in a fast-moving startup where processes are still being built

• Experience working with B2B SaaS customers; eCommerce, Shopify ecosystem, DTC, or order tracking software experience is a plus.
• Comfortable using CRM and support tools such as HubSpot, Intercom, Zendesk, Gorgias, or similar platforms.

Nice to Haves
• Familiarity with post-purchase, returns, order tracking products
• Experience supporting SMB or founder-led eCommerce brands.
• Basic data skills in Excel, Google Sheets, or HubSpot reporting.

Benefits

Starting Pay: Canadian dollar 80-120K + Commission, depends on experiences, open to negotiation

401(k)

PTO

Paid Holidays

Insurance