Head of Operations & Customer Success

Hiring on behalf of our client:

Title: Head of Operations & Customer Success

Location: Toronto, Ontario, Canada

Work Arrangement: Hybrid – Approximately 3 days per week in the office

Employment Type: Full-time

Base Salary: CAD $160,000 - $180,000 per year

Performance Bonus: 15%–20%, based on outcomes

On-Target Compensation: CAD $184,000 - $216,000 per year

About the Company

Our client is an established Canadian immigration and citizenship services business with a history spanning nearly 50 years. The organization has helped individuals worldwide access Canadian immigration information, resources and professional legal services.

The company is now undergoing a significant transformation toward an AI-native legal technology operating model. Following approximately fivefold growth over six months, the organization is scaling from around 60 employees to more than 100. To support this next phase, our client is seeking a Head of Operations & Customer Success to establish scalable people operations, strengthen client satisfaction and introduce more efficient, technology-enabled workflows.

About the Role

Reporting directly to the Chief Operating Officer, you will lead the development of the company's People Operations and Customer Success functions. This is a hands-on leadership opportunity with significant ownership over operational processes, systems, tooling and team development.

You will identify operational challenges, implement scalable solutions and help the business grow efficiently while maintaining high standards of service and performance.

Key Responsibilities

People Operations & Recruitment

• Build scalable people operations processes covering recruitment, onboarding, offboarding, payroll administration, leave management and performance reviews.
• Establish an in-house recruitment function capable of supporting high-volume hiring.
• Develop consistent compensation structures, performance expectations and employee processes.
• Support organizational growth through efficient workforce planning and operational improvements.

Customer Success & Service Quality

• Lead customer satisfaction initiatives across five legal practice areas.
• Monitor customer satisfaction (CSAT), Google reviews, complaints and service quality indicators.
• Establish structured processes for managing client complaints and escalations received through email and client portals.
• Investigate recurring service issues, identify root causes and implement sustainable improvements.
• Reduce escalation rates and improve the overall client experience.

Operational Systems & AI Automation

• Identify opportunities to streamline workflows through AI, automation and improved technology.
• Evaluate process improvements before recommending additional headcount.
• Develop reporting and performance metrics to support data-driven decisions.
• Help improve operational systems, including potential administration of Clio.

Team Leadership & Culture

• Build and lead teams across Talent Acquisition, Human Resources and Customer Success.
• Establish clear performance standards, accountability and professional expectations.
• Coach and develop team members while supporting a high-performance culture.

Required Qualifications

• Approximately 4–10 years of relevant experience in operations, people operations or customer success, including leadership responsibilities.
• Experience supporting or leading operational functions within a fast-growing business.
• Strong analytical and systems-thinking skills, with the ability to identify root causes and implement scalable solutions.
• Demonstrated ability to improve processes, introduce structure and manage operational change.
• Experience managing teams, establishing performance standards or developing operational functions.
• A practical, technology-oriented approach to improving efficiency through automation.
• Ability to work on a hybrid basis in Toronto, Ontario, approximately three days per week.
• Legal authorization to work in Canada without employer visa sponsorship.

Preferred Qualifications

• Experience scaling an organization from an early stage to approximately 100–200+ employees.
• Background in startups, professional services, legal services or high-volume consumer businesses.
• Experience building internal recruitment, people operations or customer success functions.
• Familiarity with AI automation tools, operational reporting or customer satisfaction platforms.
• Experience with Clio or similar business management systems.

Previous legal industry or Clio experience is not required.