Senior Enterprise Customer Success Manager in Toronto

About Us

AfterShip, a Great Place to Work Certified company, is transforming the global eCommerce landscape. Founded in 2012, AfterShip is a post-purchase SaaS company on a mission to build the world’s leading automation platform for ecommerce merchants. AfterShip unifies shipping & labels, order tracking, AI predictive delivery, and returns management into one system—giving merchants a single place to manage and automate everything that happens after checkout.

Your Mission:

We succeed when our customers succeed. Customer Success is not only a critical function at AfterShip, but a core value of the organization. As a Senior Enterprise Customer Success Manager, you'll own a portfolio of some of AfterShip's most strategic and commercially important accounts, including some of the industry's top DTC brands. These are our highest-value relationships, and you'll be trusted to protect and grow them. This role goes beyond adoption and support. You'll lead complex commercial conversations, drive renewal and expansion outcomes, and build durable relationships across every level of the customer organization, from day-to-day operators to the executive suite.

What You’ll Do:

• Own the end-to-end success of a portfolio of AfterShip's most strategic accounts, carrying direct responsibility for Net Dollar Retention, minimize churn and expansion targets.
• Lead commercial negotiations for renewals, upgrades, and multi-year agreements, partnering with Sales and leadership to structure deals that protect revenue and deepen the partnership.
• Build and execute proactive renewal strategies well ahead of contract dates, identifying risk early and mobilizing internal resources to defend and grow accounts, including in competitive situations.
• Develop multi-threaded stakeholder maps across your accounts, cultivating champions and building trusted relationships with economic buyers and executive sponsors.
• Prepare and present executive-level business reviews (QBRs/EBRs) that connect AfterShip's impact to the customer's business outcomes, using account performance metrics, industry insights, and ROI narratives to influence decision-makers and surface incremental opportunities.
• Act as the strategic voice of your customers internally, working cross-functionally with Sales, Support, Product, and Engineering across time zones to remove blockers and shape the product roadmap.
• Lead onboarding for new strategic clients in close collaboration with implementation counterparts, ensuring time-to-value is fast and measurable.
• Mentor and raise the bar for the broader CSM team, sharing best practices on commercial conversations, executive engagement, and business review craft.
• Be willing to travel for onsite client meetings, executive sessions, and trade events (up to 20%).

Who We're Looking For:

• 5+ years of experience in Customer Success, Account Management, or a related customer-facing role in SaaS, preferably in eCommerce, with a track record of managing strategic or enterprise-tier accounts.
• Proven expertise in commercial negotiations and renewals, including navigating procurement, structuring pricing conversations, and defending revenue in competitive situations.
• Demonstrated ability to own a revenue number, with a history of strong retention and expansion performance against quota.
• Exceptional executive presence and stakeholder management skills, with experience building relationships and influencing at the VP and C-suite level.
• A strong storyteller who can build and deliver business reviews that land with executives, translating data into a clear narrative about value, ROI, and opportunity.
• Ability to understand and explain technical solutions in business terms to both clients and internal stakeholders.
• Comfortable managing complex, multi-stakeholder accounts with competing priorities, and skilled at prioritization in a growth-paced environment.
• Excellent written and verbal communication and presentation skills.

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: AfterShip is built on curiosity, creativity, and collaboration.
• Ambitious Mission with Real Impact: Join us in transforming eCommerce by making buying and selling easier for everyone.
• Thrive & Grow: There’s no ceiling to what you can achieve or learn here.
• 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.

Perks:

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

Salary range for this role: CAD$141,000 - $172,000 on-target earnings.