Head of Customer Success

Accountabilities:: 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.