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.

They are hiring a

Head of Operations & Customer Success to report directly to the COO, with full ownership over people operations and customer success across five practice areas.

Why You Should Join

Direct Executive Autonomy:

Step into a blank-canvas leadership role reporting directly to the COO with zero bureaucratic red tape.

Exceptional Growth & Stability:

Experience hyper-growth (5x in 6 months) backed by the resilience and cash flow of a profitable, non-VC-funded business.

AI-First Mandate:

Real authority to deploy automation tools and AI workflows rather than defaulting to hiring more headcount.

Total Compensation:

CAD $160,000 – $180,000 base salary, outcome-based bonus (OTE ~CAD $200,000), adaptable vacation, and comprehensive health, dental, and wellness benefits.

What You'll Do

Architect People Operations:

Build talent acquisition for high-volume roles from scratch, establish transparent compensation bands, and oversee onboarding, payroll, performance management, and retention frameworks.





Own Client Satisfaction:

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

Reduce Escalations:

Build an airtight intake and resolution framework for client issues across portal and email channels, driving down escalation rates per 100 active files.

Automate Workflows:

Leverage AI automation and legaltech platforms to streamline internal processes before adding headcount.

Shape High-Performance Culture:

Recruit, coach, and set the professional benchmark for an expanding cross-functional team in HR, recruiting, and client success.

Qualifications

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.

Must be legally authorized to work in Canada

(Citizen or PR); able to work hybrid out of the Toronto office (~3 days/week)

#J-18808-Ljbffr

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