Director, Customer Success (B2B SaaS)

TL;DR

Director, Customer Success (B2B SaaS): Driving retention, expansion, and long‑term customer value across a strategic Enterprise portfolio with an accent on operational excellence and team leadership. Focus on mitigating churn risk, accelerating time‑to‑value, and scaling customer success programs for high-ARR accounts.

Location: Hybrid, Toronto, Canada

Salary: $160,000 - $189,000 (Base)

Company

Employee recognition and rewards platform empowering organizations to build cultures where people feel seen and valued.

What you will do

• Manage a strategic book of 60-80 North America-based Enterprise customers with $40M-60M ARR.
• Lead and develop a team of 8-10 Enterprise Customer Success Managers and Customer Strategy Leads.
• Own key metrics including Net Revenue Retention (NRR), Gross Retention, and ARR growth through expansion.
• Partner with Sales, Product, and Marketing to influence roadmap decisions based on customer trends.
• Build and optimize scalable programs and playbooks to enhance the customer lifecycle and time-to-value.
• Network and align with VP and C-Suite stakeholders to ensure demonstrated ROI and business value.

Requirements

• 8+ years of experience in Customer Success or Account Management within B2B SaaS.
• 5+ years of people leadership experience managing managers and senior-level ICs.
• Proven track record of owning and improving retention and customer health metrics.
• Strong operational and project management capabilities for executing at scale.
• Deep understanding of SaaS business models, renewals, and recurring revenue dynamics.
• Must be based in Toronto for hybrid work in the Liberty Village office.

Culture & Benefits

• Health benefits and life insurance coverage starting on the first day.
• Employer-matched RRSP contributions and parental leave top-up.
• Flexible vacation policy to support work-life balance.
• Professional development opportunities via LinkedIn Learning and mentorship.
• Internal Recognition and Rewards program to celebrate impact.
• Employee-led Resource Groups celebrating diversity and inclusion.