[Hiring] Senior Technical Project Manager @Thinkific

Role Description

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.

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.

Qualifications

• 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.
• Genuinely technical. They don’t need to write code, but understand how software is built and what makes an architecture decision hard.
• AI-fluent. They actively use AI tools (Claude, Copilot, Cursor, Notion AI, or similar) in their day-to-day work.
• 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.
• Experienced with modern delivery frameworks (Agile, Scrum, Kanban).
• 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.

Requirements

• 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.

Benefits

• An amazing team of talented, passionate, and kind Thinkers.
• 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.
• Comprehensive health benefits starting on Day 1, including health, vision, and dental coverage, and mental health care.
• 3 Paid Volunteer Days each year to give back to your community.
• Flexible Work options, including remote work.
• AI tools for every Thinker.
• An annual $2,000 CAD Learn and Grow fund for professional development.
• A home office setup with a company-owned Macbook Pro and budget for accessories.
• A place where you can bring your whole self to work.