Senior Product Manager in Winnipeg

We’re looking for a Senior Product Manager (Pricing & Packaging) to join Thinkific. You will own and drive the strategy, roadmap, and execution for how Thinkific’s customers manage pricing, packaging, billing, and partner integrations. Your mission is to help our creators—from solo entrepreneurs to complex B2B customers—sell and monetize their expertise with maximum flexibility and minimal friction.

You’ll ensure our solutions meet the needs of high-tier customers who demand sophisticated billing models, scalable packaging options, and seamless API integrations for partnerships. Reporting to the Senior Director, Product you will work cross-functionally with Engineering, Design, Marketing, Sales, Finance, and Customer Success, as well as directly with customers, to deliver solutions that increase revenue for our customers and Thinkific. Your goal will be to optimize Thinkific’s pricing and packaging to drive revenue growth, improve customer acquisition, and maximize lifetime value.

Here’s how you’ll accomplish this:

• Develop a compelling vision and strategy for Pricing & Packaging, aligned with Thinkific’s goals of empowering creators to grow their businesses at scale.
• Understand our customers by conducting deep research into customer jobs-to-be-done, particularly for higher-tier B2B use cases with advanced billing, packaging, and partnership needs.
• Build, communicate, manage and prioritize a clear roadmap that addresses customer pain points and opportunities in pricing flexibility, billing workflows, bulk editing, and partner API management.
• Deliver customer value by working closely with Design and Engineering, to deliver solutions that are intuitive, robust, and adaptable to varying customer business models.
• Drive business outcomes by ensuring pricing and billing capabilities directly support customer revenue growth while improving Thinkific’s own monetization opportunities (e.g., payments, plan upgrades).
• Partner with Marketing and Sales to ensure effective go-to-market plans, and with Finance and Legal to address compliance and operational needs in billing and payments.
• Collaborate with other Product Managers across Thinkific to understand upstream and downstream dependencies, identify integration points and use cases, and ensure cohesive platform-wide solutions.
• Define and deliver partner-facing APIs and tools that allow integrations with billing, payment, and distribution partners.
• Define clear success metrics (e.g., revenue lift, adoption rates, churn reduction) to analyze performance, gather feedback, and iterate.
• Advocate for best practices in pricing strategy, billing workflows, and API design. Champion customer-centric thinking across Thinkific.

The person we have in mind likely:

• Has 5+ years in SaaS Product Management with a track record of shipping and growing products that handle complex billing, pricing, packaging, or payments workflows.
• Demonstrates strong monetization expertise, including designing pricing models, managing billing systems, or working on payments products in SaaS or eCommerce environments.
• Is customer-obsessed, with proven experience deeply understanding customer needs—especially B2B use cases requiring scale, bulk editing, and flexible integrations.
• Has an API and platform mindset, with experience delivering APIs and managing third-party integrations, ideally in billing, payments, or partner ecosystems.
• Is a data-driven decision maker, comfortable turning qualitative and quantitative data into clear product priorities and business cases.
• Balances strategic and tactical skills, able to define big-picture vision while delivering incremental value quickly in an agile environment.
• Is an excellent communicator, capable of aligning diverse stakeholders, writing clear specs, and explaining complex billing concepts in simple terms.
• Has demonstrated cross-functional leadership, working effectively with Engineering, Design, Marketing, Sales, Finance, and Customer Success teams.
• Is adaptable and resilient, thriving in a fast-paced environment with changing priorities and able to navigate ambiguity while making sound decisions with imperfect information.
• Has experience as an agile practitioner, participating in agile development environments and ceremonies.
• Loves to learn and grow. They’ve found (and keep looking for) ways to level up their skills in this field, whether that’s through formal education, gaining professional experience, or maybe even building their own business.

These things would also be nice, but we think you could learn them on the job:

• Familiarity with global payment systems, tax/VAT compliance, or subscription billing platforms (e.g., Stripe, Chargebee, Recurly).
• Experience with B2B SaaS sales motions and enterprise customer requirements.
• Knowledge of pricing experimentation, such as A/B testing and tier design.
• Interest in AI’s role in pricing, personalization, or automation.

The recruitment compensation range for this position is $110,000 – $145,000 CAD. Your specific compensation within this range is determined based on your job-related skills, knowledge, experience, and our internal equity assessment.

Diversity, Equity, Inclusion and Belonging & Accessibility: This is just our initial idea of who we’re looking for! At Thinkific, we know that people have unique career journeys. If your experience is close to what we’ve described but you feel that you might be missing a few of the requirements, please still apply! We believe in equal opportunity and are committed to diversity, equity, inclusion, and belonging across every facet of our business. We’re also committed to providing a comfortable and accessible interview experience for every candidate. If there are any accommodations our team can make throughout our hiring process (big or small), please let us know.