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Open nowFirst seen 5 days ago

Head of Operations & Customer Success

Success Matcher210 open roles

Pay
CA$160,000 – CA$180,000 a year
Where
Toronto, ON, Canada
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Your applicationOpen nowHead of Operations & Customer SuccessSuccess Matcher · Toronto, ON, Canada

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: first seen 5 days ago

The posting

Our client is Canada's leading legal and immigration platform, combining a 50-year legacy of profitable success with the velocity of an AI-native scale-up. Millions of people engage with their digital resources each month, and following a recent pivot to AI-driven operations, the organization has achieved 5x growth in just six months on its mission to build the country's largest consumer law practice.

They are seeking a versatile Head of Operations & Customer Success to report directly to the Chief Operating Officer. In this role, you will hold dual ownership over people operations and customer success across five core practice areas, architecting the operational systems that will scale the company from 60 to 100+ team members.

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, 15% – 20% 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.

Required Experience

  • More than 4 years of progressive leadership experience across operations, customer success, or people operations in a fast-paced tech, legaltech, or professional services environment.
  • Proven track record building internal HR, high-volume recruiting pipelines, and operational systems from zero to one.
  • Practical experience managing customer sentiment (CSAT, NPS, public reviews) and designing resolution pathways for client escalations.
  • Strong builder mindset with demonstrated use of AI automation tools, modern CRMs/practice management platforms, and data-driven systems.
  • Legal authorization to work in Canada (Citizen or Permanent Resident) and ability to work hybrid out of the Toronto office (3 days/week).
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