Customer Success Manager

Remote (Canada)

Job Details

Travel: Occasional travel required approximately 2–3 times per year

Base Salary: CAD $70,000-$80,000 per year

Target Variable Incentive: CAD $10,000-$20,000 per year

About the Role

This opportunity is for a proactive and growth-oriented Customer Success Manager who will own strategic customer relationships and help clients achieve measurable business outcomes. The role is responsible for driving product adoption, account expansion, customer retention, successful renewals, and long-term partnerships across a portfolio of strategic accounts.

The Customer Success Manager will act as a trusted advisor to senior executives, finance leaders, human resources stakeholders, and program administrators. The position requires confidence in executive-level conversations, strong commercial judgement, and the ability to connect customer goals with practical recommendations that support growth, compliance, and operational efficiency.

This role is well suited to someone who enjoys solving high-impact challenges, working in a fast-paced SaaS environment, and using customer data to demonstrate value and influence strategic decisions.

What You’ll Do

Drive Customer Value and Growth

• Own a portfolio of strategic customer accounts and deliver measurable outcomes that strengthen customer return on investment.
• Lead consultative onboarding and successful program implementations using established playbooks and processes.
• Ensure alignment with executive stakeholders throughout onboarding and implementation.
• Drive revenue growth across the portfolio through increased adoption, program optimization, successful renewals, and account expansion.
• Monitor customer engagement, program performance, and usage trends to confirm that customers are receiving ongoing value.
• Identify and pursue opportunities to expand programs within existing accounts based on customer goals, usage insights, and organizational changes.

Build Trusted Customer Partnerships

• Develop strong relationships with executives, program administrators, human resources leaders, finance partners, and other key stakeholders.
• Act as a proactive and trusted advisor throughout the customer lifecycle.
• Lead executive business reviews and Quarterly Business Reviews focused on measurable value, performance insights, and growth opportunities.
• Use data-driven storytelling to communicate results, demonstrate value, and influence customer decisions.
• Anticipate customer needs and address challenges before they affect adoption, retention, or renewal outcomes.

Deliver Long-Term Customer Outcomes

• Create and execute customer engagement strategies that deepen adoption, sustain long-term value, and strengthen loyalty.
• Manage end-to-end renewal cycles, including customer discussions, negotiation of terms, and efforts to secure multi-year commitments where appropriate.
• Work proactively with customers to resolve challenges and ensure programs continue delivering value before renewal periods begin.
• Partner with leadership to improve customer segmentation, success playbooks, and scalable customer success frameworks.
• Collaborate with Product, Sales, Operations, and Support teams to improve internal processes and provide a seamless customer experience.
• Represent customer needs internally while maintaining alignment with broader growth objectives.

Own Renewal Readiness and Retention

• Lead renewal conversations for accounts within the assigned portfolio.
• Drive retention and successful renewals through proactive account planning and customer engagement.
• Monitor customer health indicators and identify early signs of risk, disengagement, or reduced value realization.
• Develop action plans to address customer concerns and reduce renewal risk.
• Ensure customers continue receiving measurable value throughout the full relationship lifecycle.

Qualifications

• Three to five years of experience in a customer-facing role such as Customer Success, Account Management, or Consulting, preferably within a SaaS environment.
• Demonstrated experience managing mid-sized to large enterprise accounts involving multiple stakeholders.
• Proven success driving customer retention, product adoption, renewals, and account expansion across a diverse portfolio.
• Experience leading customer onboarding, implementation, business reviews, strategic planning sessions, renewal discussions, and expansion conversations.
• Confidence communicating with C-level executives and influencing high-stakes business decisions.
• Strong analytical and strategic thinking skills, including the ability to synthesize information and turn customer data into actionable recommendations.
• Ability to use metrics and data-driven storytelling to demonstrate value and influence outcomes.
• Strong negotiation skills, including experience discussing renewal terms and longer-term commitments.
• Customer-centred and commercially minded approach, with a focus on long-term value and account growth.
• Strong organizational skills and attention to detail when managing complex programs, negotiations, and stakeholder expectations.
• Self-motivated and comfortable taking ownership in a fast-paced, high-growth environment.
• Collaborative approach and the ability to contribute effectively within a high-performing cross-functional team.
• Strong technical aptitude and experience working successfully in a remote-first environment.

Benefits

• Remote work and flexible working hours.
• Mentorship and professional development opportunities.
• Extended medical and dental benefits.
• Healthcare spending account.
• CAD $3,000 annual health and wellness spending account.
• Employee assistance program.
• Flexible unlimited time off with no annual vacation cap, supported by a trust-based approach to time away.