Staff Product Manager- Remote

As a leading InsurTech, we make getting the right coverage simple, fast, and accessible through a digital-first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.

At our client, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change.

If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!

We’re hiring a Staff Product Manager to help shape the future of our products and drive company-wide impact! This is a senior-level, subject-matter-expert role that combines strategic vision with hands-on leadership across multiple teams.

The Product team works to design, develop, and manage user-centered digital products that align with our business goals. Through close collaboration with stakeholders, user feedback, and data-driven insights, we deliver innovative and reliable solutions that move the business forward.

Reporting to the Director of Product, you’ll define and deliver a 2–3 year product strategy that aligns with the company’s long-term vision. You’ll work closely with Product and Engineering leadership to shape development practices, influence roadmaps, and ensure consistent product direction across teams.

As an individual contributor and domain expert, you’ll raise the bar for Product Management through mentorship, technical depth, and scalable processes that promote fact-based problem solving and continuous improvement.

This is a remote-first role within the GTA. #LI-Remote

Advantages
What You Bring:
A thoughtful, data-driven approach to decision making and the confidence to prioritize what matters most.
A genuine passion for developing the product craft and problem-solving skills of other product managers.
Clear and persuasive communication skills, especially when working with executives and cross-functional teams.
You can work independently, navigate ambiguity with ease, and deliver results.
Strategic thinking with a systems mindset, anticipating how today’s decisions shape tomorrow’s outcomes.
A collaborative and growth-oriented mindset with a passion for mentoring and elevating other Product Managers.

Responsibilities
Responsibilities:
Act as a strategic thought leader, creating clear and inspiring narratives that align teams and stakeholders around a shared product vision.
Define, own, and gain buy-in for the 2-3 year product vision of the assigned domain, and develop a concrete 18-24 month strategy and roadmap that ensures alignment with the overall product and business strategy.
Collaborate with Product leaders to co-develop and optimize the overarching 18-24 month product strategy and roadmap.
Partner with Product leadership to shape cross-domain priorities, coordinate resources, and maintain alignment across multiple teams.
Serve as the strategic hub and arbiter for product and development teams, resolving significant dependencies and conflicting priorities to drive successful delivery.
Lead end-to-end problem solving from strategy to execution, balancing business and technical needs to maximize impact and ROI.
Proactively identify high-value opportunities, assess risks, and align stakeholders on the best path forward.
Collaborate with Engineering leadership to ensure the future state of the product and technical strategy aligns with long-term goals.
Establish and share best practices that strengthen strategic planning and execution across the Product team.
Partner with Product and Engineering leaders to raise the organization’s overall strategic and delivery capabilities.
Mentor Product Managers on advanced discovery, stakeholder alignment, and strategic execution.

Qualifications
Requirements:
University degree or college diploma in a recognized technical, vocational or academic program (preferably in Engineering or Computer Science) or equivalent work
10+ years of experience in digital or software Product Management.
5+ years of experience as a senior individual contributor or an equivalent role in Product Management, with proven hands-on experience leading and implementing company-wide strategic initiatives across multiple product domains and teams.
Proven success owning the full product lifecycle, from 0 to 1 through scale, ideally in a complex, customer-facing platform or self-serve digital product.
Strong ability to dive into technical architecture, understand complex data flows, and make informed decisions about platform, infrastructure, and APIs.
Skilled in building and executing product strategy and long-term roadmaps that tie to business outcomes.
Deep understanding of strategic frameworks, linking day-to-day execution with long-term company value.
Advanced experience in feature planning, resource management, and prioritization across multiple teams.
Proven track record of improving and scaling product processes in collaboration with product leadership.
Strong discovery skills, consistently identifying the right problems, validating with data, and applying structured frameworks.

Summary
What You Bring:
A thoughtful, data-driven approach to decision making and the confidence to prioritize what matters most.
A genuine passion for developing the product craft and problem-solving skills of other product managers.
Clear and persuasive communication skills, especially when working with executives and cross-functional teams.
You can work independently, navigate ambiguity with ease, and deliver results.
Strategic thinking with a systems mindset, anticipating how today’s decisions shape tomorrow’s outcomes.
A collaborative and growth-oriented mindset with a passion for mentoring and elevating other Product Managers.

Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.

Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.