Director of Customer Success

Job Description

We are looking for a Director of Customer Experience to rebuild and own our customer support and retention function from the ground up. Customer service is currently highly manual and overloaded, and we need a senior leader to design the strategy, build the team, and implement the systems that deliver an exceptional, scalable customer experience across Canada and the US.

Key Responsibilities

• Strategy & Design: Own the end-to-end customer experience strategy for Canada and the US (50/50 business split). Audit current processes and SLAs to design a best-in-class support model.
• Team Leadership: Build and lead a high-performing customer service and customer retention team (hiring, coaching, and performance management).
• Systems & Automation: Define and implement tools and workflows (e.g., Zendesk, NPS, macros, routing, self-serve/FAQ, templates).
• Metrics & Reporting: Establish and track core CX metrics (NPS, CSAT, response/resolution time, first contact resolution, and retention/repeat purchase metrics). Create insights and present recommendations to leadership.
• Retention Growth: Partner closely with Marketing to design and execute loyalty and retention programs that increase LTV and repeat purchase rate.
• Operational Playbooks: Develop playbooks for handling escalations, VIP customers, peak-season volume, and social/D2C support.
• Cross-Functional Collaboration: Partner with Operations, Logistics, and Production to proactively address customer issues and bring the customer voice into product and marketing decisions.

Requirements

• Experience: 7+ years in customer experience, customer service, or CX operations, including 3+ years leading teams.
• Scaling Success: Proven experience building or significantly scaling a customer service org from scratch or early stage.
• Regional Knowledge: Experience supporting both Canadian and US customers, with an understanding of different expectations and buying behaviors.
• Technical Proficiency: Strong track record implementing and optimizing CX tools and automation (Zendesk experience preferred).
• Results-Oriented: Demonstrated success improving NPS/CSAT, response times, and customer retention.
• Strategic Mindset: Data-driven approach to defining KPIs, building dashboards, and designing loyalty programs for DTC/ecommerce brands.
• Soft Skills: Excellent people leadership, strong collaboration skills, and a high degree of grit.
• Adaptability: A bias toward action and comfort with ambiguity; thrives in a builder role with limited existing structure.

Nice to Have

• Experience in DTC, ecommerce, or consumer brands.
• Experience integrating customer service with social support (IG, TikTok, etc.).
• Experience with customer journey mapping and CX design.
  
  

What Success Looks Like (First 12 Months)

• Roadmap: Clear CX strategy, org design, and roadmap in place.
• Team: New customer service and retention team hired and ramped.
• Performance: Response and resolution times significantly reduced; NPS/CSAT materially improved.
• Efficiency: Core automations and workflows implemented in Zendesk or similar tools.
• Impact: Loyalty and retention initiatives launched with measurable impact on repeat purchase rate and LTV.