Senior Customer Success Manager

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior Customer Success Manager in Canada.

This role is an opportunity to join a fast-growing SaaS environment that is redefining how the branded merchandise industry operates through a connected workflow platform. You will act as a trusted strategic partner to enterprise customers, ensuring they achieve maximum value from the platform while driving long-term adoption, retention, and growth. Working in a remote-first and highly collaborative culture, you will engage with clients to understand their business goals, guide them through onboarding and expansion, and help translate technical capabilities into meaningful business outcomes. You will also serve as a key bridge between customers and internal Product, Engineering, Sales, and Support teams, ensuring feedback directly shapes product evolution. This is a high-impact role where relationship management, technical curiosity, and strategic thinking come together. You will play a direct part in improving customer success outcomes and influencing the direction of a category-defining platform.

• Serve as the primary strategic partner for a portfolio of enterprise customers, driving engagement, retention, and long-term success
• Lead onboarding, training, and ongoing enablement for new and expanding enterprise accounts
• Conduct regular business reviews to align customer goals with platform capabilities and identify opportunities for deeper adoption
• Act as a technical advisor for API and webhook integrations, troubleshooting issues and supporting solution design discussions
• Monitor customer health, identify churn risks, and proactively drive expansion and upsell opportunities
• Gather and translate customer feedback into actionable insights for Product and Engineering teams
• Collaborate cross-functionally with internal teams to improve customer experience and optimize success processes
• Contribute to internal initiatives aimed at improving scalability, automation, and efficiency within Customer Success workflows

Requirements:

• 3+ years of experience in Customer Success, Account Management, or a similar role within a SaaS or technology environment
• Strong technical aptitude with the ability to understand and troubleshoot APIs, webhooks, and integration-related topics
• Experience working with CRM or Customer Success tools such as Salesforce, Gainsight, or equivalent platforms (a plus)
• Excellent communication and relationship-building skills, with the ability to influence senior stakeholders
• Strong analytical mindset with a data-driven approach to managing account health and performance
• Comfortable working independently in a remote and asynchronous environment while maintaining strong collaboration with teams
• Ability to think strategically while also executing tactically in a fast-paced environment
• Interest or experience working with AI-driven tools is an advantage
• Bonus: familiarity with the promotional products or creative agency industry, or ability to build basic proof-of-concept solutions

Benefits:

• Competitive annual salary range of CAD 87,500–95,000 plus CAD 15,000 commission target
• Fully remote-first work environment across Canada (excluding Quebec)
• Health and dental benefits, including a healthcare spending account
• Retirement savings contributions (RRSP/TFSA) up to CAD 3,000 annually
• Company-wide paid closure from December 25 to January 1
• Twice-yearly in-person company summits and team events
• Flexible, collaborative, and high-trust remote culture
• Opportunity to work in a fast-scaling SaaS company shaping an entire industry