Director of Customer Success

About Us

AfterShip, a Great Place to Work Certified company, is transforming the global eCommerce landscape. Our mission is to empower retailers to create the world's best online shopping experiences, from post-purchase and beyond.

We've powered more than 8 billion shipments for over 20,000 leading brands including Samsung, Gymshark, Mejuri, and TOMS. Our AI-driven post-purchase solutions span shipment tracking, returns management, personalized product discovery, and delivery predictions with industry-leading accuracy.

Backed by a $66M Series B and over a decade of innovation, we're accelerating growth and defining the future of the post-purchase experience. With 450+ team members across the globe, we're building a diverse, collaborative culture that encourages agility, ownership, and impact.

Your Mission:

At AfterShip, customer success isn't just a department—it's a core value that drives our business. We win when our customers win. As Director of Customer Success, you will lead a global team of highly motivated Customer Success Managers (CSMs) across North America, Europe, and APAC, ensuring they have the tools, strategy, and leadership to help our customers thrive.

This role is critical to AfterShip's success and touches every part of the business. Your team will be the voice of the customer, working cross-functionally with Sales, Product, Engineering, and Support to ensure our customers' needs shape everything we do. You'll drive onboarding, retention, and expansion strategies while influencing product direction based on real customer insights.

The Director of Customer Success, reporting to the VP of Revenue, will lead AfterShip's global Customer Success team, driving customer retention, expansion, and satisfaction across multiple regions. This remote-first role is open to candidates across North America, with a preference for those based in the Greater Toronto Area. At AfterShip, we value results over rigid structures, giving you the flexibility to manage your schedule in a way that best supports your team and customers. Collaboration is key, and while the role is primarily remote, there will be opportunities for in-person engagement on a cadence that enhances productivity and connection. Travel may be required (up to 20%, fully expensed) to meet with customers, attend leadership offsites, or support key business initiatives.

What You'll Do:

• 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.

Who We're Looking For:

• 7+ 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.

At AfterShip, we understand that not all applicants will have skills that match the job description exactly. We value diverse experiences and respect that experience comes in many different forms, so even if you feel you may not meet every qualification to a T then we still encourage you to apply. We are always looking for people who can help us continue to raise the bar for our team and who want to join us on our mission.

Why You Should Join Us:

• 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. 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.

Perks:

• Competitive compensation
• Remote-first/hybrid-flexible work setups
• Healthcare coverage offered from day 1
• Retirement plans including company match
• Annual learning & wellness benefit
• Monthly book perk
• Career progression & professional development
• In-office lunch and commuter benefits for those located in our hub locations

We are an equal opportunity employer. In addition, we are committed to providing accommodations for applicants upon request at any stage of the recruitment process in accordance with the legislative requirements of this job's location. Please let us know if you require accommodation due to a disability during any aspect of the recruitment process and we will work with you to address your needs.

Director of Customer Success

Toronto

Customer Success