Senior Legal Counsel in Winnipeg

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 experience, 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 1,200 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.

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.

AfterShip is seeking an accomplished commercial lawyer to join our Global Legal team as Senior Legal Counsel, Commercial. As commercial deal volume, value, and complexity have grown materially, this role is a targeted investment to strengthen our commercial contracting capability in North America.

Reporting to the General Counsel, you will independently lead complex, high-value commercial negotiations, own commercial escalation frameworks, and advise North American leadership on commercial strategy and risk. You will also serve as a senior mentor to other members of the commercial legal team, helping them grow into more complex and strategic work.

This role sits within AfterShip's Global Legal team, working alongside colleagues based in the EU and building out coverage for North America. Because the team collaborates closely with colleagues in Europe and APAC, this role may occasionally require working outside of regular business hours for team meetings or cross-regional collaboration.

What You'll Do

• Contracts & Negotiations: Independently draft, review, and negotiate complex, high-value commercial agreements, including enterprise customer contracts, vendor and partnership agreements, and NDAs; own commercial escalation frameworks and resolve complex contractual disputes.
• Commercial Strategy & Risk Advisory: Advise North American business leadership, GTM, and Product teams on commercial strategy, risk positions, and deal structuring; act as a trusted legal business partner in high-stakes negotiations.
• Mentorship & Talent Development: Provide senior-level mentorship to junior and mid-level commercial counsel, calibrating risk positions and building the internal capability needed to handle increasingly complex matters.
• Global Coverage & Collaboration: Partner with Legal colleagues across the EU and APAC to maintain seamless, follow-the-sun commercial coverage and support handoff continuity across time zones.
• Process, Templates & Legal Operations: Contribute to the ongoing evolution of contract templates, negotiation playbooks, and Legal Operations initiatives that improve efficiency and consistency across the commercial function.

Who We're Looking For

• J.D. or equivalent law degree, and an active license to practice law in the U.S. or Canada;
• 7+ years of relevant legal experience, including significant in-house commercial counsel experience (SaaS or technology industry strongly preferred);
• A track record of independently leading complex, high-value commercial negotiations with minimal oversight;
• Strong knowledge of commercial contracting and technology/SaaS agreements, with working familiarity with data privacy and IP considerations a plus;
• Demonstrated experience mentoring and developing junior legal talent;
• Excellent judgment and business acumen, with the ability to communicate complex legal concepts clearly to non-legal stakeholders;
• Ability to work autonomously and collaboratively in a fast-paced, distributed, global team environment.

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. We're a passionate, global team of problem solvers who put egos aside to innovate together.
• 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. 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.
• Competitive compensation, 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.

Salary range for this role: CAD$131,000 - 150,000.

We are an equal opportunity employer and provide accommodations upon request throughout the recruitment process, in accordance with local legislation.