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.
About CWILL
CWILL (pronounced "quill") is a post-purchase and retention suite built for Shopify brands. We help merchants reduce support tickets, recover lost revenue from returns, and turn one-time buyers into loyal fans - with tools purpose-built for every touchpoint that follows the sale.
www.cwill.com
The Role
- CWILL is hiring a Customer Success Manager to own merchant relationships for two core post-purchase products: Order Tracking and Returns & Exchanges.
- You will be the primary point of contact for a portfolio of eCommerce merchants using these tools - guiding them through onboarding, driving adoption, resolving issues, and making sure they're getting real business value. This is a hands-on, customer-facing role where you'll work closely with merchants, the CS Lead, and internal product and engineering teams.
- The ideal candidate is customer-obsessed, comfortable discussing tracking workflows and returns flows with a merchant ops team, and thrives in a fast-moving startup where some processes are still being built.
Onboarding & Adoption
- Guide new merchants through setup and configuration of CWILL's Order Tracking and Returns & Exchanges products
- Help merchants understand and activate key features: branded tracking pages, carrier integrations, automated return rules, exchange flows, and refund policies
- Identify early adoption risks and proactively help customers reach their first value milestone faster
- Maintain onboarding checklists and enablement materials for common merchant segments
Account Management & Retention
Manage a portfolio of SMB and mid-market merchants as their main point of contact for both products
Monitor account health signals: tracking page engagement, return request volume, exchange rates, carrier success rates, and churn risk indicators
Run regular merchant check-ins focused on business outcomes - reduced WISMO tickets, improved return conversion, faster resolution times
Surface upsell and cross-sell opportunities, including plan upgrades and expansion to additional CWILL products
Support & Issue Resolution
- Triage merchant issues related to tracking accuracy, carrier data delays, return portal errors, or exchange flow configuration - coordinating with engineering through to resolution
- Identify recurring support themes and route them as structured product feedback
- Maintain high standards for responsiveness, follow-through, and documentation
Insights & Collaboration
- Capture merchant feedback, feature requests, and competitive insights from daily conversations
- Share customer context with Product to inform roadmap priorities for both Order Tracking and Returns
- Keep CRM records, account health notes, and lifecycle stages accurate and up to date
What We're Looking For
- Bachelor's degree or equivalent practical experience.
- 2–4 years in Customer Success, Account Management - ideally at a SaaS or shipping 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.
Starting Pay: Canadian dollar 80-120K + Commission, depends on experiences, open to negotiation
401(k)
PTO
Paid Holidays
Insurance
CWILL is an equal opportunity employer. We evaluate candidates on the skills and track record the role requires, and welcome applicants from all backgrounds.
