Director, Customer Success

Achievers; Toronto; Hybrid; CAD 223,000 - 264,000; Full time

Benefits offered by this job

Hybrid flexibility

Toronto office presence

Health benefits & life insurance

RRSP contributions

Parental leave

Job summary

Achievers is seeking a Director, Customer Success to drive retention, expansion, and long-term value across a NA Enterprise portfolio. You will lead 8-10 Enterprise CSMs/CSLs, focusing on churn mitigation, revenue growth, and high product adoption.

The role partners with Sales, Product, Marketing, Support, and Professional Services to scale outcomes. The ideal candidate is a hands-on leader who thrives in fast-moving environments, rigorously manages KPIs, and inspires teams to deliver repeatable

Qualifications

• 8+ years in Customer Success or related revenue-retention roles in B2B SaaS.
• 5+ years of people leadership managing managers and senior ICs.
• Proven track record of owning retention, expansion, and customer health metrics.
• Strong operational and project management capabilities with scale.
• Experience cross-functionally with Sales, Product, and Engineering.
• Deep understanding of SaaS renewals and recurring revenue dynamics.
• Exceptional communication with senior customer leaders and internal stakeholders.

Responsibilities

• Own customer success outcomes across a defined book of business.
• Lead and develop a high-performing team of Enterprise CSMs and CSLs.
• Mitigate churn risk using data-driven signals and qualitative insight.
• Drive ARR growth through expansion, cross-sell, and value realization.
• Partner with Sales, Product, Marketing, Support, and Professional Services.
• Translate strategy into scalable customer programs and playbooks.
• Forecast accuracy and renewal management with rigorous metrics.
• Engage with VP and C-Suite leaders to align on outcomes.

Skills

People leadership

Customer Success

Data-driven

Cross-functional collaboration

KPI management

Tools

CRM systems

Data analytics tools

Job description

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 trendsWork 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

Why Achieversis a Great Place to Work

At Achievers, we believe recognition is a powerful driver of connection. With more than 4.3 million users across 190 countries, our employee recognition and rewards platform empowers organizations to build cultures where people feel seen and valued, everyday. We’re a team of passionate, thoughtful builders who care deeply about our product, our customers, and each other. Visitachievers.com to see how we’re inspiring recognition everywhere.

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 Perk for permanent full-time employees:

• Rewardsfor your impact through our Recognition and Rewards program
• HealthBenefits and Life Insurance Coverage beginning on your first day
• ParentalLeave Top-up
• Employer matched RRSPcontributions
• FlexibleVacation to recharge, so you can bring your best
• Employeeand Family Assistance Programoffering mental health, legal, and financial counselling
• Supportedprofessional development and career growth(Linkedin Learning, mentorship)
• Employee-Led Employee Resource Groupsthat celebrate our diversity
• Regular events designed to build connection, belonging, and well-being
• Hybridflexibility, with time in our beautiful Liberty Village, Toronto office

Achievers is proud to be an equal opportunity employer committed to building a diverse, inclusive workplace where everyone can do their best work. We encourage qualified candidates from all backgrounds and experiences to apply.

Achievers is committed to ensuring an inclusive and accessible recruitment process for all candidates. If you require any accommodations for your interview, such as assistive technology, wheelchair accessibility, or alternative formats of materials, please let us know. We are happy to make necessary arrangements to support your needs