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 contemporary 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

1. An exploratory call with our Talent team
2. An impact-focused interview with Manager, Program Management
3. Technical Stage
4. 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 ⭐

📌 Senior Technical Project Manager (Canada)
🏢 Thinkific
📍 Canada