Fast Facts

Join Top Hat as a Group Product Manager to lead the strategic vision for the Questions and Gradebook domain and drive platform integration initiatives while mentoring a team of Product Managers.

Responsibilities: Define long-term product strategy, execute product lifecycle from ideation to launch, build cross-functional relationships, and conduct customer research to inform product direction.

Skills: 5+ years of product management experience, technical fluency in SQL, strong execution abilities, data-driven decision making, and exceptional collaboration across teams.

Qualifications: Experience in EdTech or SaaS, with a background in assessment platforms or learning management systems, and a history of managing complex product initiatives.

Location: Remote work environment with headquarters in Toronto, Canada.

Compensation: Not provided by employer. Typical compensation ranges for this position are between CAD 120,000 - CAD 160,000.

We are looking for a Group Product Manager who can own and drive the strategic direction of our Questions and Gradebook domain, alongside platform integration initiatives. This role requires someone who can execute flawlessly while thinking strategically, build coalitions across teams, and represent the product vision to executive leadership.

You'll be responsible for key domains of the Top Hat platform, serving millions of students and thousands of instructors in higher education, leading a team of 2-3 Product Managers. This is a high-impact, high-visibility role where your decisions directly influence both product strategy and business outcomes.

What You'll Do

• Strategic Leadership:
• Define and champion the long-term product vision, strategy, and roadmap for our domains revolving our assessments and student learning experience, ensuring alignment with company objectives and market opportunities
• Drive product-market fit and sustainable competitive advantage through continuous customer research, market analysis, and strategic positioning
• Act as thought leader and portfolio representative to executive leadership, cross-functional partners, and external stakeholders
• Develop compelling business cases that connect product investments to revenue, retention, and strategic value
• Execution Excellence:
• Mentor PMs on the complete product lifecycle from ideation through launch and iteration, shipping high-quality products on time, leading by example
• Move fast with strong judgment on value vs. risk tradeoffs—make swift decisions without analysis paralysis
• Maintain technical independence: spin up MVPs quickly, pull data directly from databases, and validate hypotheses rapidly
• Actively participate in sprint ceremonies focused on scoping, prioritization, and retrospectives
• Cross-Functional Collaboration & Influence:
• Build strong partnerships with Engineering, Design, Data, GTM, Customer Success, and Marketing teams
• Lead through influence, not authority—build coalitions and align stakeholders proactively
• Facilitate cross-functional collaboration with clarity, creating environments where teams love working with you
• Recruit and manage customer design partners for pilots and validation
• Innovation & Customer Obsession:
• Embrace rapid prototyping and experimentation—build, test, learn
• Conduct customer discovery, validate with real users early and often
• Foster a high-performance culture defined by innovation, accountability, and customer obsession
• Support and mentor other Product Managers in research, market analysis, and identifying unmet customer needs

What We're Looking For

Must-Haves:

• 5+ years of product management experience, with 1+ years in a management role
• Technical fluency: Comfortable with SQL/data queries, able to spin up MVPs independently or with minimal eng. Support
• Track record of shipping complex, cross-functional products on time and at high quality
• Exceptional execution: You finish what you start, don’t let things fall through the cracks, and are known for reliability
• Fast decision-making with strong judgment on importance/value vs. risk
• Business-first thinking: You optimize for company success, not just your team
• Data-driven and goal-oriented: You define clear metrics and consistently hit targets
• Outstanding cross-functional collaboration: Engineering, Design, GTM teams enjoy working with you
• Experience building business cases with financial projections, ROI analysis, and strategic value articulation
• Experience with AI-assisted development tools, for work or personal projects

Strong Preferences:

• Experience in EdTech, SaaS, or B2B2C business models
• Background in assessment platforms, learning management systems, or educational content
• History of leading integrations or complex multi-product initiatives
• Proven ability to influence without authority and resolve cross-team conflicts
• Experience with rapid prototyping and AI-assisted development tools
• Portfolio thinking: Can articulate unified strategy across multiple interconnected products

What makes you exceptional:

• You think strategically but execute tactically—comfortable in both modes
• You embrace experimentation and aren't afraid to prototype and iterate quickly
• You're extremely responsive and get things done in record time
• Marketing, CS, and GTM teams call out how much they love working with you
• You proactively identify problems before they become blockers
• You communicate with clarity: stakeholder updates are clear, actionable, and well-documented
• You maintain strong external relationships
• You have strong opinions, loosely held—you challenge respectfully when you disagree
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• This role is tailored for someone who brings exceptional execution, collaboration, and strategic thinking. We value finishers who move fast, thrive in uncertainty, disrupt the status quo, and make everyone around them better.

Why team members love working at Top Hat:

• A noble mission that creates meaningful, fulfilling work
• A team that cares deeply for customers and for each other
• Flexible, remote first work environment
• Professional learning and development for all role levels
• An awesome and welcoming Toronto HQ
• Competitive health benefits that start on day one
• A management team focused on performance, growth, engagement and connection
• Our winning strategy and market potential
• Innovative PTO policy with lots of time and space for self-care
• Passionate customers that believe in us—and what we do
• A chance to work with new tech like generative AI—and see the customer impact