Director, Customer Success

Accountabilities:: Lead, manage, and develop the Account Management team, fostering a high-performance culture built around customer satisfaction, accountability, collaboration, and continuous improvement. Own customer retention, contract renewals, and expansion revenue across a portfolio of enterprise accounts, ensuring long-term customer value and sustainable business growth. Develop and maintain strong, trusted relationships with senior customer stakeholders, particularly within large enterprise and international retail organizations. Monitor customer health, engagement, and satisfaction indicators, proactively identifying potential risks and implementing strategies to improve retention and prevent churn. Identify opportunities for account growth, upselling, and cross-selling while aligning customer objectives with broader commercial priorities. Partner with the VP of Customer Success to evolve organizational structures, account coverage models, and operational processes as the business expands. Lead organizational transformation and operational improvements to increase team productivity, scalability, and consistency across the customer experience. Champion the adoption of AI-powered tools, automation, and emerging technologies to streamline workflows, improve team capacity, and strengthen customer outcomes. Collaborate closely with Sales, Product, Revenue Operations (RevOps), and other cross-functional teams to represent customer needs and ensure alignment on business priorities. Act as a senior decision-maker, independently navigating complex customer and operational challenges while identifying practical, commercially sound solutions. Support the development and optimization of global Customer Success operations, ensuring consistent service quality across different regions and time zones. Coach and mentor Account Management leaders and team members, supporting professional development, succession planning, and leadership growth. Lead teams through organizational changes, maintaining engagement, transparency, and alignment around strategic objectives. Establish clear performance expectations and accountability frameworks to ensure the team consistently delivers strong customer relationships, retention results, and expansion revenue. Travel when required, potentially up to 25% of working time. Requirements: Significant leadership experience in enterprise SaaS Customer Success, Account Management, or a related commercial function. Proven experience managing managers and developing high-performing teams within complex enterprise customer environments. Demonstrated success driving customer retention, contract renewals, customer satisfaction, and expansion revenue within a high-touch customer success model. Experience leading and scaling global or multi-region teams, including managing organizational transformations and evolving customer coverage strategies. Strong commercial and business acumen, with the ability to balance customer relationship management, strategic priorities, and revenue objectives. Excellent leadership, coaching, and mentoring capabilities, with a track record of developing talent and building accountable, collaborative teams. Strong stakeholder management and communication skills, with the ability to influence senior executives and collaborate effectively across multiple departments. Sound judgment, strategic thinking, and the ability to make independent decisions in a fast-paced and evolving business environment. Previous experience working in a scaling SaaS organization, ideally within a business generating between USD 30 million and USD 100 million in annual recurring revenue (ARR). Ability to collaborate effectively across international time zones, particularly with teams and customers based in North America and Europe. Adaptability and resilience, with the ability to lead through change while maintaining team engagement and operational performance. Additional qualifications considered an asset: Experience working alongside customer support or technical support teams. Background in retail technology or familiarity with retail store operations and frontline workforce management. Knowledge of Customer Success and CRM platforms such as Gainsight, Catalyst, or Salesforce. Experience implementing AI-driven tools and automation to improve customer success processes, reporting, and team productivity. Experience managing strategic enterprise accounts and working with internationally recognized brands. Benefits: Annual salary range: CAD 184,714–225,762, depending on experience, qualifications, skills, and location. Stock options offering meaningful ownership in a fast-growing, venture-backed technology business. Fully remote-first working environment, providing flexibility to work from wherever you are most productive. Flexible paid time off policy, allowing employees to take time away when needed. Monthly coffee-shop stipend to support flexible working arrangements and alternative workspaces. Fully paid one-month sabbatical after five years of service. Comprehensive medical, dental, and vision insurance coverage. Quarterly paid volunteer day to support a nonprofit organization of your choice. Unlimited access to Udemy Business for professional development, training, and continuous learning. Annual company-wide off-site events in international destinations, offering opportunities to connect and collaborate with colleagues. Collaborative, inclusive, and supportive remote working culture. Opportunities to work with talented professionals across different countries and backgrounds. Strong focus on employee well-being, professional growth, and meaningful contributions. Potential international travel opportunities as part of the role.