Senior Technical Project Manager in Winnipeg

Thinkific (TSX: THNC) is an award-winning learning commerce platform built for scale. By bringing together community, courses, and content with commerce, we power transformative learning experiences and give businesses everything they need to grow their revenue — all from one AI-powered platform.

The culture we're building is recognized as an award-winning culture—we’re a Certified Great Place to Work, one of Canada's Best Diversity Employers, BC Top Employers, and Canada's Top Small & Medium Employers for 2026 by Canada's Top 100!

Here’s what it means to work at Thinkific: We're a high-performing team on a meaningful mission, and the way we work reflects that. Thinkers are customer-obsessed and ownership-driven — we talk to customers constantly, take full accountability for outcomes, and operate with a high degree of autonomy and trust. We care deeply for each other and believe the best ideas come from honest debate, real feedback, and diverse perspectives.

Who thrives here: Thinkific may be the right place if you're energized by a fast-paced environment, enjoy high autonomy, and work well with ambiguity and change. You thrive in highly collaborative teams and make the people around you better. You're results-driven, take ownership without being asked, have hard conversations even when it's uncomfortable, and celebrate diverse perspectives.

About the Role: Are you energized by complex, cross-functional challenges? We’re looking for a Senior Technical Project Manager to join us at Thinkific. This role sits within our Program Management team inside Research & Development — a small but mighty team that operates at the heart of how Thinkific delivers.

Your goal will be to drive end-to-end delivery of complex, cross-functional initiatives and raise the bar on how we ship. Here’s how you’ll accomplish this:

• Own end-to-end delivery of high-stakes initiatives, leading programs that cut across engineering, product, data, and go-to-market teams from scoping through launch.
• Build and maintain strong relationships with stakeholders at every level — engineers, product managers, executives, and external partners.
• Leverage AI as a force multiplier.
• Translate business objectives into executable project plans by identifying dependencies, sequencing work intelligently, and proactively flagging when scope, timeline, or resources need to shift.
• Anticipate problems before they become blockers.
• Define and reinforce standards for how we ship — quality gates, rollout plans, retrospectives, and post-mortems that actually lead to change.
• Own executive-level AI-assisted reporting with clear, opinionated status updates, risk dashboards, and decision-ready briefings.

The person we have in mind likely:

• Has 5+ years of experience in technical project management or program management.
• Is genuinely technical.
• Is AI-fluent.
• Is a systems thinker who holds the whole picture.
• Communicates with clarity and confidence.
• Is experienced with modern delivery frameworks (Agile, Scrum, Kanban).
• Is data-informed and uses metrics to track progress and make decisions.
• Loves to learn and grow.

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

• Experience in a B2B SaaS or learning product company.
• Familiarity with evaluating and rolling out AI tooling within engineering or product teams.
• PMP, PgMP, or equivalent certification.
• Experience managing vendor relationships or third-party integrations at scale.

The recruitment compensation range for this position is $93,100 – $116,400 – $139,700 CAD (this range is base salary only). Your specific compensation within this range is determined based on your job-related skills, knowledge, experience, and our internal equity assessment.

The Hiring Journey includes an exploratory call with our Talent team, an impact-focused interview with the Manager, Program Management, a Technical Stage, and a Stakeholder Interview with the VP, Research & Development.

Diversity, Equity, Inclusion and Belonging & Accessibility: 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.

What you can expect if you join Thinkific: An amazing team of talented, passionate, and kind Thinkers. Together, we’ve built an incredible award-winning culture. A competitive compensation package including base salary, equity, team-wide bonuses, and an Employee Share Purchase Plan. Flexible Paid Time Off to maintain mental and physical health. Health Benefits and Wellness: Comprehensive benefits starting on Day 1 include health, vision, and dental coverage for you and your family.