Head of Client Success and Operations

This is a fully remote position, open to applicants in Canada, +2 more states.

📋 Description

• Lead and mentor a team of 15–30 Customer Success Managers (CSMs) and coaches focusing on onboarding, retention, and renewal calls.

• Recruit, train, promote, and terminate staff — developing middle management as the team expands.

• Address refund, chargeback, and escalation issues to maintain client relationships and protect revenue.

• Take ownership of key performance indicators (KPIs) related to retention, renewals, and outcomes — providing daily reports.

• Enhance scripts, processes, and standard operating procedures (SOPs) to ensure scalability.

• Collaborate with Sales and Marketing teams to identify and resolve underlying issues.

• Manage the Coaching/Delivery Department comprehensively.

⛳️ Requirements

• Demonstrated experience leading teams of 20+ individuals in a high-touch, outcome-oriented service industry (coaching, education, professional services, high-ACV customer success, health coaching, or a similar field).

• Proven ability to develop systems, SOPs, and scorecards from the ground up.

• Excellent skills in objection handling, retention calls, and preventing refunds/chargebacks.

• A proactive mindset — willing to engage directly with clients rather than merely overseeing staff.

• Strong sense of ownership over your department, treating it as if it were your own business.

• Familiarity with AI and SaaS tools.

🏝️ Benefits

• Compensation is negotiable based on experience, with flexibility.

• Base salary is also negotiable depending on experience.

• Opportunities for performance-based commissions.

• Potential for equity upside.