Director, Customer Success

Accountabilities: Lead, coach, and develop the Account Management team, fostering strong customer relationships, accountability, collaboration, and continuous improvement. Own customer retention, renewal, and expansion outcomes across a portfolio of enterprise accounts, ensuring customers consistently realize value from the platform. Monitor customer health, identify potential risks, and proactively implement strategies to protect retention and uncover growth opportunities. Partner with senior Customer Success leadership to evolve team structures, customer coverage models, and operational processes as the business scales. Lead organizational and operational changes that improve efficiency, team effectiveness, and the overall customer experience. Champion the adoption of AI, automation, and emerging technologies to streamline workflows, increase team capacity, and improve customer outcomes. Collaborate closely with Sales, Product, Revenue Operations, and other cross-functional teams to represent customer needs and align business priorities. Act as a trusted decision-maker, independently navigating complex challenges and driving effective solutions with sound judgment. Support the development of consistent, high-quality Customer Success operations across global regions. Coach and mentor Account Management leaders and team members, supporting professional growth, succession planning, and leadership development. Lead teams confidently through change, maintaining engagement, alignment, and focus on business and customer outcomes. Travel as required, potentially up to 25% of the time. Requirements: Significant leadership experience in enterprise SaaS Customer Success or Account Management, including experience managing managers. Proven track record of driving customer retention, renewals, and expansion revenue within a high-touch enterprise customer model. Experience leading and scaling global or multi-region teams, including managing organizational change and evolving customer coverage strategies. Strong commercial acumen, with the ability to balance customer relationships, business priorities, and revenue objectives. Demonstrated ability to build and develop high-performing teams, influence cross-functional stakeholders, and make independent decisions. Experience working in a scaling SaaS organization, ideally within the $30M–$100M annual recurring revenue (ARR) range. Ability to collaborate effectively across global time zones, particularly with teams and customers in North America and Europe. Nice to have: Experience working alongside Customer Support or Technical Support functions. Background in retail technology or familiarity with retail store operations. Familiarity with Customer Success and CRM platforms such as Gainsight, Catalyst, or Salesforce. Experience using AI and automation to improve Customer Success operations. Benefits: Annual base salary range of CAD $184,714–$225,762, depending on experience, location, and relevant skills. Stock options, providing an opportunity to share in the company's growth. Fully remote working model with a remote-first culture. Flexible time-off policy. Monthly coffee-shop stipend to support flexible working arrangements. Fully paid one-month sabbatical after five years of employment. Comprehensive medical, dental, and vision coverage. Annual company off-sites and opportunities to connect with colleagues in person. One paid day per quarter for volunteering with a nonprofit organization of your choice. Unlimited access to Udemy Business for continuous learning and professional development. Opportunities to work with a collaborative, globally distributed team. Inclusive working environment that values diverse backgrounds, experiences, abilities, and perspectives.