Enterprise Account Executive

AfterShip; Toronto; Remote; CAD 266,000 - 407,000; Full time

Benefits offered by this job

Healthcare coverage

Unlimited PTO

Remote-first culture

Annual learning & wellness benefit

Job summary

AfterShip is seeking an Enterprise Account Executive to win new logos among top ecommerce retailers in North America. You will craft strategies for named accounts, secure access to senior executives, and lead multi-month, multi-product deals from first meeting to signature.

Collaboration with Marketing, RevOps, and Success teams is key. The role is remote-first with hub locations in North America and Canada, and may require occasional non-standard hours for global coordination.

Qualifications

• 5+ years of full-cycle SaaS closing experience
• Experience selling to VP and C-level leaders
• Hunter mindset: opened doors at target accounts
• Proficiency with CRM tools like HubSpot and Gong

Responsibilities

• Own new business across a named list of enterprise retailers and D2C brands
• Build and run account plans for target lists
• Earn meetings with senior leaders across ecommerce, CX, operations, and finance
• Lead discovery mapping post-purchase stack and build business cases
• Navigate security, legal, and procurement reviews for multi-year deals
• Collaborate with Solutions Architects, Product Marketing, and Success teams

Job description

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

AfterShip's North American go-to-market team is in a growth phase. Our largest opportunity sits with enterprise retailers and D2C brands, where post-purchase spans multiple carriers, regions, storefronts and teams - and where unifying shipping, tracking, and returns on one platform creates the biggest impact.

As an Enterprise Account Executive, you will win new logos among the largest eCommerce merchants in North America. You will build strategies for a named list of target accounts, earn access to senior executives, and lead complex, multi-stakeholder sales cycles from first meeting through signature. Deals are larger, longer and multi-product, typically running 6+ months and involving security, legal, and procurement review.

You will work alongside Marketing, Professional Services, RevOps, and Customer Success to land and set up long-term partnerships. This is a remote-first position, with a preference for candidates in the United States (New York, California, Utah, Texas) or Canada (Toronto). This role requires collaboration with teams located in Asia and Europe, which may require working outside of regular business hours 1-2 times per week.

What You’ll Do

• Own new business across a named list of enterprise eCommerce retailers and D2C brands, from account research through negotiation and close
• Build and run account plans for your target list, pairing your own executive outreach with BDR, marketing, and partner-sourced pipeline
• Earn meetings with senior leaders across eCommerce, Customer Experience, Operations, Supply Chain, and Finance, and multi-thread to reach the economic buyer early
• Lead consultative discovery that maps the merchant's post-purchase stack, quantifies the cost of the status quo, and builds an executive business case tied to support costs, shipping spend, return rates, and repeat purchase revenue
• Qualify rigorously using a structured framework (such as MEDDICC) and drive deals with mutual action plans that keep champions, buyers, and timelines aligned
• Orchestrate the deal team, partnering with Solutions Architects on technical discovery, integrations, and tailored demos, and with Product Marketing on competitive strategy
• Navigate security reviews, legal redlines, and procurement, and negotiate multi-year, multi-product agreements
• Work with ecosystem partners such as Shopify Plus, commerce agencies, and system integrators to source and accelerate deals
• Own an accurate forecast in HubSpot and use Gong to review your calls and act on coaching
• Represent AfterShip in person at executive meetings, onsites, and industry events
• Hand off closed customers cleanly to Onboarding and Customer Success, setting them up for adoption and expansion

Who We're Looking For

• 5+ years of full-cycle SaaS closing experience, including 3+ years selling to enterprise accounts, with a documented record of hitting or exceeding quota
• A history of closing six-figure, multi-stakeholder deals with sales cycles of six months or longer
• Experience selling to VP and C-level leaders, and building business cases that win approval from Finance and procurement
• A structured, repeatable sales process you can walk us through, including how you qualify, multi-thread, and build mutual action plans
• Confidence navigating security questionnaires, legal redlines, and complex procurement processes
• Hunter mindset: you have opened doors at target accounts with no existing relationship, and you don't wait for inbound to fill your pipeline
• eCommerce, retail tech, or logistics experience strongly preferred, along with a working understanding of the Shopify Plus ecosystem and enterprise commerce platforms
• Proficiency with HubSpot or a comparable CRM, plus Gong, LinkedIn Sales Navigator, and modern sales engagement tooling
• High coachability and ownership: you seek feedback, review your own calls, and set your own rhythm without being told
• Ability to travel up to 20%
• You've sold post-purchase, shipping, returns, CX, or supply chain software to enterprise retailers
• You've built relationships with Shopify Plus partners, commerce agencies, or system integrators
• You've sold a platform or multi-product suite, not only a single point solution
• You've worked at a company scaling into the enterprise segment and helped shape the playbook

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

On-target-earnings (OTE) range for this role: $190,000 - 290,000

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.