Head of Customer Success

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Head of Customer Success based in Canada. We are seeking an experienced customer success leader to oversee a global Customer Success, Implementation, and Support function within a growing enterprise SaaS environment. In this senior leadership role, you will own strategic customer relationships, retention performance, customer advocacy, and the voice of the customer across the business. You will lead and develop a team of 10 professionals while establishing scalable processes that support continued growth. Working closely with executive leadership, Product, Engineering, and commercial teams, you will translate customer insights into meaningful business and product improvements. You will also drive customer retention, strengthen operational performance, and help deliver successful enterprise implementations across global markets. This remote opportunity offers significant influence over company strategy, customer experience, and the future direction of the product.

Strategic Customer Relationships: Build and maintain trusted, executive-level relationships with key enterprise customers, ensuring strong engagement, satisfaction, and long-term partnerships. Retention and Revenue Growth: Own Gross Revenue Retention (GRR) and Net Revenue Retention (NRR) performance, identify renewal risks and expansion opportunities, and partner with commercial teams to support sustainable growth. Customer Advocacy: Maintain strong customer referenceability and develop strategies that encourage customer advocacy, testimonials, and long-term loyalty. Voice of the Customer: Establish effective processes for collecting, consolidating, and prioritizing customer feedback, translating insights into actionable recommendations for Product and Engineering teams. Product Collaboration: Partner with Product Management to influence roadmap priorities and ensure product development addresses customer needs and improves outcomes. Team Leadership and Development: Lead, mentor, and develop a global team of Customer Success, Implementation, and Support professionals. Establish clear performance expectations, career development pathways, and future hiring plans. Scalable Customer Operations: Develop playbooks, workflows, and resources that standardize best practices throughout the customer lifecycle, from implementation and onboarding to ongoing support and renewals. Enterprise Implementation and Escalations: Support complex global rollouts by coordinating across customer stakeholders and internal teams. Strengthen account planning, customer health monitoring, risk management, escalation handling, and executive engagement. Executive Reporting: Provide regular updates to executive leadership on customer health, retention, advocacy, support performance, risks, and growth opportunities, translating operational data into clear recommendations. Requirements: Customer Success Leadership: 10+ years of experience in Customer Success supporting technology products, with a strong track record of leading enterprise customer relationships. Enterprise Customer Experience: Proven experience supporting large enterprise organizations and Fortune 500 customers, including complex stakeholder environments and high-value accounts. Strategic Communication: Excellent written and verbal communication skills, with the ability to build credibility and communicate effectively with C-level executives. Cross-Functional Collaboration: Experience working closely with Product Management and the ability to represent customer needs, influence product priorities, and advocate for improvements that support customer success. Customer Retention Expertise: Strong understanding of customer retention, renewal management, account health, risk identification, and expansion opportunities. Team Management: Ability to lead, mentor, and develop customer-facing teams while establishing performance standards and scalable operating practices. Organization and Execution: Strong organizational skills, sound judgment, and the ability to manage multiple priorities and workstreams in a fast-paced environment. Industry Familiarity: Familiarity with transportation, parking, workplace technology, or related enterprise technology solutions. Remote Collaboration: Ability to work remotely while supporting collaboration across US time zones, from the Pacific Coast to the East Coast. Location and Time Zone: Candidates must be based in Canada or the United States, with a preference for those in Eastern or Central time zones. Benefits: Competitive Compensation: Competitive salary, equity participation, and benefits. Leadership Influence: Direct access to executive leadership and the opportunity to help shape business strategy and company direction. Product Impact: A central role in influencing the development of a platform that addresses complex workplace, parking, and transportation challenges. Global Enterprise Exposure: The opportunity to build relationships with innovative, high-profile enterprise organizations across multiple industries. Remote Flexibility: Work remotely from Canada or the United States without needing to relocate. Career Growth: Lead and scale a global Customer Success function within a growing enterprise SaaS environment. Collaborative Culture: Join a values-driven team that prioritizes customer outcomes, collaboration, and mutual support.