Department: Product

Employment Type: Full Time

Location: Canada - Remote

Compensation: $130,000 - $160,000 / year

Description Who We are: At Wagepoint, we’re good people. Sure, maybe we’re biased. But that’s only because Wagepointers bring the best versions of ourselves to do some of the best work in our careers.

We’re an authentic team who bring our diverse backgrounds, ideas, experiences and cultures together to make payroll magic. Speaking of, we “pull rabbits out of hats” for thousands of small business owners across Canada who rely on our payroll software to pay their employees and process their payroll taxes. And we’re just getting started.

We’re growing and looking for more awesome people to join our merry band of misfits. We are looking for people who share our understanding that when it comes to our commitment to our customers: we mean business. Especially given that the consequences of getting payroll wrong can sometimes be dire.

If you are the kind of person who has always wanted to make a difference and be heard at work, Wagepoint will give you plenty of opportunity to do just that.

The Role At High Level Wagepoint is seeking a Senior Product Manager who will bring depth of experience in product discovery, executional excellence, and outcome measurement. In this role, you will shape product strategy and roadmaps, drive discovery practices that uncover real customer needs, and ensure delivery processes consistently produce measurable business and customer outcomes.

You’ll play a pivotal role in strengthening how Wagepoint’s product, design, and engineering teams collaborate, introducing processes and frameworks that raise execution quality across the organization. You will help establish product management best practices, mentor other PMs, and influence how the company scales its product discipline during this growth stage.

Your work will directly support Wagepoint’s mission to deliver reliable, delightful payroll for small businesses, where accuracy is critical, and great product design builds trust.

What You'll Be Expected To Own Customer Discovery & Insight

• Lead discovery practices that uncover real customer needs, using tools like Gong, Zendesk and Pendo.
• Build structured approaches for synthesizing insights and ensuring customer voices drive strategy, not just features.
• Develop friction maps and VOC spotlights that influence roadmaps and executive decision-making.

Product Strategy & Roadmaps

• Translate company OKRs and customer insights into product strategies and multi-quarter roadmaps.
• Prioritize initiatives that balance customer value, business outcomes, and technical feasibility.
• Deliver strategy docs, product narratives, and outcome-focused plans that align stakeholders at all levels.

Product Delivery & Executional Excellence

• Own end-to-end product delivery for major product areas, from discovery through launch and post-release iteration.
• Establish and mature frameworks for planning, estimation, and execution, ensuring predictable and high-quality delivery.
• Ensure every initiative has success metrics defined up front and tracked consistently post-launch.

Stakeholder Alignment & Communication

• Partner with executives, engineering, design, and GTM leaders to create shared clarity on priorities, trade-offs, and outcomes.
• Provide crisp updates, product briefs, and roadmaps that inspire confidence and drive alignment across teams.

AI-Enabled Product Management

• Champion the adoption of AI to accelerate discovery, insight synthesis, and delivery processes.
• Evaluate and introduce AI tools and workflows that enhance team productivity and decision-making.
• Model best practices for how AI can be leveraged strategically (not just tactically) in product development.

What You Bring To The Table

• 5–8 years of product management experience, with multi-company exposure preferred, and a track record of impact in SaaS, B2B, or compliance-adjacent domains.
• Proven success owning strategic product areas or full product lines, not just features.
• Strength in product discovery — customer empathy, validation methods, and translating insights into strategy.
• Demonstrated ability to create or mature executional frameworks (roadmaps, OKRs, rituals, discovery, experimentation).
• Strong communication and storytelling skills, able to engage executives, cross-functional peers, and frontline teams.
• A metrics-driven mindset, comfortable designing KPIs, running experiments, and measuring outcomes.
• Experience mentoring or coaching PMs and influencing cross-functional partners.
• AI-curious, leveraging tools to accelerate discovery, analysis, and delivery.

What We Bring To The Table

• Impact: Roll up your sleeves and directly contribute to the growth and success of Wagepoint by shaping our workforce.
• Culture: The opportunity to work with the world’s friendliest team, solving interesting problems together with an endless amount of laughter (We work hard, but we always have time for a bad joke or two).
• Growth: Opportunities for professional development and career advancement - we are always, always learning with a growth oriented mindset.
• Innovation: Work in an environment that encourages creativity and new ideas.
• Remote: The ability to work from home, forever! Wagepoint is a remote company, so you don’t have to worry about commuting to an office. Plus, more time with your pets is always a bonus!

Ready to embark on an exciting journey with us? Apply now and help us build the future of Wagepoint!