Our client is Canada’s premier legal and immigration platform, pairing a 50-year profitable foundation with an AI-native operational model. With millions of monthly visitors and 5x growth in the past six months, they are scaling from 60 to 100+ team members to build the country’s largest consumer law firm. Head of Operations & Customer Success to report directly to the COO, with full ownership over people operations and customer success across five practice areas.

Experience hyper-growth (5x in 6 months) backed by the resilience and cash flow of a profitable, non-VC-funded business. CAD $160,000 – $180,000 base salary, outcome-based bonus (OTE ~CAD $200,000), flexible vacation, and comprehensive health, dental, and wellness advantages. Build talent acquisition for high-volume roles from scratch, establish transparent compensation bands, and oversee onboarding, payroll, performance management,



and retention frameworks.

Monitor and elevate CSAT and public review scores across all five practice disciplines, diagnosing root causes behind low scores to implement lasting fixes.

Shape

High-Performance Culture: More than 4 years leading operations, customer success, or people operations in a fast-paced or scale-up environment. Proven track record building internal HR, recruiting, and operational infrastructure from scratch.

Experience managing client retention, CSAT/reviews, and root-cause escalation frameworks. Practical fluency with AI automation tools and modern practice management/CRM systems. Citizen or PR); able to work hybrid outof the Toronto office (~3 days/week) #

📌 Head Of Operations & Customer Success (Winnipeg)
🏢 Success Matcher Recruitment
📍 Winnipeg