About this role.
Thinkific is seeking a Senior Technical Project Manager to lead complex, high-stakes initiatives across engineering, product, data, and go-to-market teams. The role owns delivery from scope through launch, including dependency management, risk mitigation, quality gates, rollout planning, and executive reporting. The successful candidate brings at least five years of technical project or program management experience in a software or SaaS environment, plus strong knowledge of modern delivery frameworks. This is a fast-paced, highly autonomous role that expects AI fluency, sound judgment under ambiguity, and clear communication with both technical and executive stakeholders.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader CA market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would explain the business objective, the teams involved, the delivery plan, and the measures of success. I would highlight how I mapped dependencies, established decision forums, surfaced risks early, and used launch and post-launch metrics to confirm the outcome.
I make the trade-offs explicit using a clear view of scope, capacity, dependencies, risk, and customer impact. I present viable options, such as reducing scope, sequencing delivery, adding resources where appropriate, or moving the date, then facilitate an accountable decision with stakeholders.
I translate the blocker into its business impact, affected milestones, risk level, decision required, and recommended path forward. I avoid unnecessary implementation detail while ensuring executives have enough context to make a timely, informed decision.
I have used AI to synthesize meeting notes, draft status updates, identify themes in risk signals, and accelerate documentation. I treat outputs as a starting point, verify accuracy, protect sensitive information, and establish team guardrails for responsible use.
I lead a blameless retrospective focused on facts, contributing conditions, and systemic improvements rather than individual fault. I convert findings into prioritized actions with owners and due dates, then track those actions to completion and assess whether they reduced recurrence.
Who we are ⬇️
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. So far, our customers have generated over $3.7 billion in revenue and reached more than 200 million learners worldwide.
The culture we’re building ⭐
We’ve been intentional about the culture we’re building and are proud to be 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. It’s a culture built on trust, exceptional work, and genuine respect for the people around us.
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. AI is a tool you embrace to move faster and think bigger.
Who doesn’t thrive here:
If you prefer highly structured environments, need to wait for clear direction to move, dislike ambiguity and change, or find direct feedback uncomfortable, Thinkific may not be the right fit.
About the Role 🚀
Are you energized by complex, cross-functional challenges — the kind where you’re the person who brings clarity to ambiguity, momentum to high-stakes initiatives, and trust to every room you walk into? 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. This team is a strategic force multiplier, owning complex end-to-end initiatives operating at the intersection of people, product, and AI-augmented delivery.
A note from the Hiring Manager
Hi! I am Afro, Manager of Program Management. I’m passionate about tackling complex cross-functional problems and excited for this person to join our team. This role is not just about organizing meetings and doing follow-ups. You will be highly engaged in owning projects end-to-end, solving interesting problems, and making meaningful decisions that contribute to Thinkific’s goals and our customers’ success. If this and a fast, AI-driven, and highly collaborative environment excites you, I can’t wait to meet you.
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. You’ll define what “done” looks like and hold the organization accountable to it
Build and maintain strong relationships with stakeholders at every level — engineers, product managers, executives, and external partners. You’ll surface trade-offs clearly, manage competing priorities, and keep everyone rowing in the same direction
Leverage AI as a force multiplier. You already integrate AI tools into how you work — drafting status updates, synthesizing risk signals, generating meeting summaries and documentation, and accelerating decision-making
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. You’ll build contingency plans, facilitate hard conversations early, and keep stakeholders informed
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, with a track record of delivering complex, cross-functional initiatives in a software or SaaS environment
Is genuinely technical. They don’t need to write code, but understand how software is built and what makes an architecture decision hard
Is AI-fluent. They actively use AI tools (Claude, Copilot, Cursor, Notion AI, or similar) in their day-to-day work. They’re comfortable helping teams define guardrails for responsible AI use in workflows
Is a systems thinker who holds the whole picture — dependencies, risks, resource constraints, business context — while staying sharp on the details that matter most
Communicates with clarity and confidence. They write concisely, adapt their message to their audience, and can explain technical blockers in plain language
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. 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:
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 range is designed to capture the full journey from developing skills to excelling in the position. Most new hires start between the minimum and midpoint, which aligns with being fully capable in the role.
The Hiring Journey
An exploratory call with our Talent team
An impact-focused interview with Manager, Program Management
Technical Stage
Stakeholder Interview with VP, Research & Development
For a deeper look at our hiring process, what to expect during each step, AI guidelines, and how to prepare, visit our Candidate Hub ⭐
How we work with AI:
Thinkific is an AI-forward company. We use AI tools across all teams, and our approach to hiring is no different. We use AI-assisted tools to support parts of our recruitment operations, and we’re committed to being transparent about how. We automate where it drives efficiency, but every hiring decision is made by a person, and a high-touch, human candidate experience always comes first.
Candidates are welcome to use AI tools during the application process if desired.
👉 Visit our Candidate Hub to learn more!
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.
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—we’re a Certified Great Place to Work and have been recognized on many Great Place to Work’s Best Workplaces lists for Canada, Technology, Inclusion, Women, Mental Wellness, and more! We’re also one of Canada’s Best Diversity Employers, BC Top Employers, and Canada’s Top Small & Medium Employers for 2026 by Canada’s Top 100!
🚀 The chance to build, improve, and innovate on a platform that’s driving positive impact for thousands of businesses and millions of students around the world.
💸 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. Our team is encouraged to take a minimum 4 weeks of vacation, plus Thinker Holidays (extended long weekends in the summer) and time off for the December holiday season.
🩺 Health Benefits and Wellness: Comprehensive benefits starting on Day 1 include health, vision, and dental coverage for you and your family, $3,000 for mental health care, a short-term health plan, and an additional $900/year health or personal spending account. Plus, family friendly benefits include generous parental leave top-ups for up to 32 weeks, as well as fertility coverage and personalized return to work options.
🤝 3 Paid Volunteer Days each year to give back to your community and support the causes you care about.
💻 Flexible Work. Choose to work from home from anywhere in Canada, at our Vancouver HQ, a co-working space, or anywhere there’s wifi for a change of scenery.
🤖 AI tools for every Thinker. We’re an AI-forward team, and every employee has access to the tools they need to work smarter, faster, and make a bigger impact.
⬆️ Learning & Growth. An annual $2,000 CAD Learn and Grow fund for conferences, seminars, or courses, plus training, mentorship, coaching, and internal promotion opportunities.
🏡 A home office setup so you’re ready to succeed with a company-owned Macbook Pro and a budget to order a desk, chair, or any accessories to help you work comfortably and productively.
💙 A place where you can bring your whole self to work. We know that different perspectives lead to amazing ideas, more innovation, and, ultimately, our success as a company. We welcome applicants of all backgrounds, experiences, beliefs, identities, and statuses. Whoever you are—we can’t wait to meet you!
The Thinkific Vancouver office operates on the traditional, ancestral, and unceded territories of the xʷməθkʷəy̓əm (Musqueam), Sḵwx̱wú7mesh (Squamish), and Sel̓íl̓witulh (Tsleil-Waututh) Nations of the Coast Salish People. We encourage everyone to learn more about the original caretakers of the land that you currently occupy.
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