The Director, Customer Success is a senior leadership role responsible for driving retention, expansion, and long-term customer value across a strategic Enterprise portfolio of B2B SaaS customers. This role owns excellence in execution-translating strategy into outcomes through disciplined operating rhythms, strong project management, and accountability to measurable results.

Your portfolio responsibility will consist of 60-80 North America-based Enterprise customers totaling $40M-60M ARR. You will lead and develop a team of 8-10 Enterprise-level Customer Success Managers (CSMs) and Customer Strategy Leads (CSLs) focused on identifying and mitigating churn risk, driving new and existing revenue, accelerating customer time-to-value, and ensuring high product utilization and adoption. This role partners closely with Sales, Product, Marketing, Support, and Professional Services to innovate and deliver exceptional customer outcomes at scale.

The ideal candidate is a hands-on leader who thrives in complex, fast-moving environments, rigorously manages performance against KPIs, and inspires teams to deliver consistent, repeatable results.

Why you'll love this role:

• Lead and scale a high-performing Customer Success team, coaching leaders and driving a culture of customer excellence.
• Make a direct business impact by owning customer retention, growth, and long-term success.
• Partner with executive stakeholders to help customers achieve meaningful business outcomes.
• Shape strategy and influence change across Product, Sales, and Operations.
• Build and optimise scalable programs that enhance customer experience and support company growth

How you'll shape Customer Operations at Achievers:

Customer Outcomes, Retention & Growth

• Own customer success outcomes across a defined book of business, with accountability for:
  • Net Revenue Retention (NRR)
  • Gross Retention / Churn
  • ARR growth through expansion, cross-sell revenue and recognition point volume and redemption margin
  • Product adoption, utilization, and value realization
• Proactively identify and mitigate customer churn-risk using data-driven signals and qualitative insight
• Ensure customers realize clear, documented business value tied to their original use cases and evolving goals
• Engage with customer leadership to deepen and broaden our connection with key stakeholders
• Lead strategies that drive revenue growth through demonstrated ROI, strong executive alignment, and outcome-based success planning
• Ability to multi-thread and network at the VP and C-Suite level of our customers' organizations

Team Leadership & Performance Management

• Lead, coach, and develop a high-performing team of Customer Success Managers and Customer Strategy Leads
• Set clear expectations, operating cadences, and performance standards aligned to company priorities
• Drive high accountability for execution, results, and forecast accuracy
• Manage customer escalations to successful resolution and correct root cause to mitigate reoccurrence
• Partner with Enablement and Revenue Operations to build and maintain scalable and durable programs to elevate team capability
• Foster a culture of ownership, urgency, and continuous improvement

Execution Excellence & Program Management

• Translate customer success strategy into operational execution across people, process, and tools
• Lead complex, cross-functional initiatives (e.g. risk mitigation, renewal transformation, adoption programs)
• Improve customer time-to-value and sustained value through program road mapping, success planning, and lifecycle engagement
• Ensure consistent use of customer success methodologies, playbooks, and best practices
• Manage capacity planning, segmentation strategy, and coverage models to scale the function effectively

Cross-Functional Leadership & Influence

• Partner with Enablement, Revenue teams, and Account Management on renewals, expansions, and account planning
• Collaborate with Product and Engineering to influence roadmap decisions through customer insight and trends
• Work closely with Support and Professional Services to deliver a seamless customer experience
• Act as a strong internal advocate for the customer while balancing business outcomes

Metrics, Insights & Reporting

• Define, track, and continuously improve key Customer Success KPIs and health scores
• Analyze data to identify trends, risks, and opportunities across segments and cohorts
• Deliver clear, actionable insights to executive leadership on customer health, retention risk, and growth potential
• Ensure rigor and accuracy in forecasting renewals and expansion revenue

Experience we feel will set you up for success:

• 8+ years of experience in Customer Success, Account Management, or related revenue-retention roles within B2B SaaS
• 5+ years of people leadership experience managing managers and senior-level ICs
• Proven track record of owning and improving retention, expansion, and customer health metrics
• Strong operational and project management capabilities with the ability to execute at scale
• Experience working cross-functionally with Sales, Product, and Engineering teams
• Deep understanding of SaaS business models, renewals, and recurring revenue dynamics
• Exceptional communication skills with the ability to engage senior customer leaders and internal stakeholders

Our Approach to Total Rewards

We're committed to providing a fair and competitive offer based on what you bring to the team. Each A-Players' compensation is reviewed at least annually against performance and impact in role. We want you to see your path to growth, understand your impact, and feel valued every step of the way.

Our customer success roles follow a defined commission structure that rewards your performance. For this role, the compensation plan follows a 70/30 split for base and commission earnings. $160,000 - $189,000 reflects the base salary range, depending on experience, skills and market data.

Benefits and Perks for permanent full-time employees:

Rewards for your impact through our Recognition and Rewards program

🩺 Health Benefits and Life Insurance Coverage beginning on your first day

Parental Leave Top-up

Employer matched RRSP contributions

Flexible Vacation to recharge, so you can bring your best

Employee and Family Assistance Program offering mental health, legal, and financial counselling

Supported professional development and career growth (Linkedin Learning, mentorship)

Employee-Led Employee Resource Groups that celebrate our diversity

Regular events designed to build connection, belonging, and well-being

CA Hybrid flexibility, with time in our beautiful Liberty Village, Toronto office