Head of Operations & Customer Success

We're Hiring: Head of Operations & Customer Success | Toronto, Canada

🏢 Work Model: Hybrid - approximately 3 days in the office

💼 Employment Type: Full-time

Our client is looking for a Head of Operations & Customer Success to help scale a fast-growing, AI-native legal tech company. This is an opportunity to build scalable systems, improve customer experience, and shape people operations as the company grows from 60 to 100+ employees.

If you're a systems thinker who enjoys solving complex operational challenges, leveraging AI automation, and building high-performing teams, this could be a great fit.

What You'll Do

• Build People Operations: Establish recruiting processes, onboarding, offboarding, performance reviews, compensation bands, payroll, and employee policies.
• Own Customer Success: Drive client satisfaction across multiple practice areas, improve CSAT scores, and strengthen the overall customer experience.
• Reduce Escalations: Build structured complaint management processes, identify root causes, and implement improvements to reduce recurring issues.
• Leverage AI & Automation: Automate workflows and streamline operations using AI tools before adding headcount.
• Build & Lead Teams: Hire, coach, and manage teams across talent acquisition, HR, and customer success.
• Drive Operational Excellence: Use data and measurable outcomes to improve processes, accountability, and performance.

What We're Looking For

• 4–10 years of experience in operations, people operations, or customer success, ideally within a fast-growing startup.
• Experience building and scaling processes in a high-growth environment.
• Strong analytical and problem-solving skills, with a focus on identifying root causes and implementing lasting solutions.
• A proactive approach to AI tools, workflow automation, and operational efficiency.
• Proven ability to hire, develop, and retain high-performing teams.
• Comfortable working in a hybrid environment in Toronto, Canada.

Experience scaling a company from approximately 20 to 100–200+ employees is a strong plus. Legal industry or Clio experience is not required.

Why This Opportunity?

• Take ownership of operations and customer success in a rapidly scaling business.
• Build people operations and customer experience systems from the ground up.
• Drive meaningful AI adoption and automation across the organization.
• Work closely with senior leadership and help shape the company's next phase of growth.

Interested or know someone who might be a great fit? Feel free to reach out or share this opportunity with your network.