Director of Customer Success

Summary

Join AfterShip, a Great Place to Work Certified company, as the Director of Customer Success and lead a global team of Customer Success Managers. You will be responsible for driving customer retention, expansion, and satisfaction across North America, Europe, and APAC. This remote-first role, based preferably in the Greater Toronto Area, requires strong leadership, strategic thinking, and cross-functional collaboration. You will own key metrics, develop customer engagement strategies, and optimize operations. AfterShip offers a flexible work setup, competitive compensation, and various benefits to support your well-being and career growth.

Requirements

• 6+ years in Customer Success or Account Management at a B2B SaaS company (experience working with multiple products and enterprise solutions preferred)
• 4+ years of people management experience. You’ve led a Customer Success department and built high-performing, cross-regional teams
• Proven ability to build and optimize customer engagement strategies. You know how to develop retention playbooks, scalable processes, and operational systems while balancing execution with long-term vision
• Data-driven decision-maker. You use metrics and automation to identify opportunities, improve efficiency, and enhance customer outcomes
• Exceptional communicator and cross-functional leader. You confidently engage with C-suite executives and enterprise customers, influencing both internal and external stakeholders

Responsibilities

• Own the success of our customers: Ensure customers achieve their desired outcomes with AfterShip, maximizing retention and expansion
• Lead and scale the Global CS team: Coach and develop a high-performing team across multiple regions, ensuring they have clear goals and the support to succeed
• Be a strategic advisor: Develop and execute customer engagement strategies that drive long-term value and advocacy
• Optimize operations & processes: Establish scalable workflows, playbooks, and automation to improve efficiency and impact
• Collaborate cross-functionally: Work closely with Sales, Product, Engineering, and Support to remove bottlenecks, drive adoption, and enhance the customer experience
• Own key metrics: Be accountable for Dollar Retention Rate, Customer Retention Rate, and expansion revenue

Preferred Qualifications

Experience working with multiple products and enterprise solutions

Benefits

• Great Place to Work Certified: We’ve been recognized for our inclusive, values-driven culture that celebrates diversity and collaboration
• Innovative & Inclusive Culture: Started by our software engineer-turned-CEO, AfterShip is built on curiosity, creativity, and collaboration. We’re a passionate, global team of problem solvers who put egos aside to innovate together. We take immense pride in fostering a culture that’s inclusive, which has allowed us to surround ourselves with the industry's most talented professionals
• Ambitious Mission with Real Impact: Join us in transforming eCommerce by making buying and selling easier for everyone. It’s one of the most dynamic spaces in tech, with limitless opportunities to innovate and grow
• Thrive & Grow: There’s no ceiling to what you can achieve or learn here. We’re committed to empowering your career while advancing together as a company
• Flexible Work Setup : We’re a remote-first team, meaning by default that employees work from home or on a hybrid-flexible basis in our hub locations (Toronto, Austin, Barcelona). You’re empowered to choose a work setup that works best for you and your team. With flexible hours depending on your time zone, you’ll be able to have a schedule that fits your working style and the requirements of your role
• Competitive Compensation – We reward top talent
• Remote-First & Hybrid Options – Work from home or a hub office
• Healthcare Coverage from Day 1 – Prioritizing your well-being
• Retirement Plans with Company Match – Invest in your future
• Annual Learning & Wellness Stipend – For courses, fitness, or self-care
• Monthly Book Perk – Expand your knowledge on us
• Career Progression & Development – Structured growth opportunities
• In-Office Lunch & Commuter Benefits – Available in hub locations