Head Of Operations & Customer Success

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), flexible 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 outof the Toronto office (~3 days/week)
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