Senior Enterprise Customer Success Manager

AfterShip; Toronto; Remote; CAD 141,000 - 188,000; Full time

Benefits offered by this job

Competitive compensation

Remote-first work setups

Healthcare coverage offered from day 1

Retirement plans including company gap

Unlimited PTO

Annual learning & wellness benefit

Monthly book perk

Career progression & professional dev.

In-office lunch and commuter benefits

Job summary

AfterShip, a Great Place to Work Certified company, seeks a Senior Enterprise Customer Success Manager in Canada. You’ll own top strategic accounts, drive renewals and expansions, and build durable CSM relationships across executive and operator levels.

You’ll influence product direction and coordinate with Sales, Support, and Engineering across time zones, with occasional after-hours meetings. Join a remote-first, globally distributed team offering flexible hours and travel up to 20% for

Qualifications

• 5+ years of experience in Customer Success or enterprise account management.
• Proven ability to negotiate renewals and expansions.
• Experience managing strategic SaaS accounts.
• Excellent executive-level communication and presentation skills.
• Ability to translate technical concepts into business outcomes.

Responsibilities

• Own end-to-end success of strategic accounts with retention and expansion targets.
• Lead commercial negotiations for renewals and multi-year deals.
• Develop renewal strategies and mobilize internal resources.
• Map stakeholders and build relationships with economic buyers.
• Prepare executive business reviews tying impact to ROI.
• Collaborate cross-functionally to remove blockers and inform product roadmap.
• Lead onboarding for new strategic clients.
• Mentor the CSM team and share best practices.
• Travel for onsite meetings up to 20%.

Skills

Executive presence

Stakeholder management

Renewals & negotiations

Strategic account management

Business reviews

Cross-functional collaboration

Storytelling with data

Time management

Job description

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. By centralizing these workflows, AfterShip enables merchants to reduce customer support inquiries, deliver a more reliable and engaging customer experiences, and unlock incremental revenue at every post-purchase touchpoint.

AfterShip integrates seamlessly with eCommerce platforms including Shopify and TikTok Shop, and connects with more than 1,400+ carriers worldwide. Today, over 20,000 businesses—including Samsung, Gymshark, Mejuri, Dr. Squatch, and Alo Yoga—rely on AfterShip to turn every post-purchase moment into an opportunity to build trust, reduce costs, and drive repeat purchases.

Built for a global market from day one, AfterShip operates with an engineering-driven, internationally distributed team. The company employs more than 450 people across 8 offices, spanning North America, Europe, and Asia, and representing over 20 cities worldwide.

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. Your ability to influence senior stakeholders, deliver compelling business reviews, and negotiate win-win commercial outcomes will directly shape AfterShip's retention and growth trajectory.

This is a high-impact position within the growing global Customer Success team. As part of a global team, there may be a need to work outside of regular office hours for meetings with Europe or APAC. Meetings outside of regular business hours are planned with advance adequate notice.

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.

At AfterShip, we know great talent doesn’t always fit every requirement. If you’re passionate about our mission and believe you can make an impact, we encourage you to apply.

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 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 - $188,000 on-target earnings

We are an equal opportunity employer and provide accommodations upon request throughout the recruitment process, in accordance with local legislation. Please let us know if you require any support, and we’ll work with you to meet your needs.

We believe in hiring right over hiring fast. While timelines may vary, we’re looking to fill this role as soon as possible.

Our hiring process uses AI to help with initial resume screening and to support interview note-taking. These tools help our team stay organized and fair, but all hiring decisions are made by people.

This job vacancy is a backfill position.