Staff Product Manager (Remote First)

About Us: Zensurance is redefining commercial insurance for Canadian businesses. 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. Zensurance has been recognized for its rapid growth and industry impact: ✅ Deloitte’s Technology Fast 50 (2023, 2024, 2025) ✅ Deloitte’s Technology Fast 500 (2024, 2025) ✅ Top Insurance Employers (2022) At Zensurance, 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 Benefits & Perks at Zensurance: At Zensurance, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success. 💻 Work Your Way • Remote-first setup for added flexibility • Home office allowance to create a comfortable workspace • Top-tier tech: "Office in a box" with all necessary tech equipment • Half days before public holidays: Enjoy half days before long weekends ❤️ Your Health, Your Way • Flexible health and dental plans for families, including mental health support • Health & personal spending accounts to invest in wellness your way • Parental leave top-up, because family comes first 🚀 Investing in Your Growth • Education assistance reimbursement for courses, conferences, books, and memberships • Opportunities to learn from industry experts and grow your career 🤝 Staying Connected • Weekly Friday huddles to share updates and connect across teams • Virtual & in-person team-building events to strengthen our culture We’re building something special. Come be a part of it! Who We Are: Business is hard work, but insurance doesn’t have to be! We empower business owners with simple, tech-driven insurance solutions through our online platform. Our success is fueled by our team-oriented culture and four core values: DELIVER – We set ambitious goals and achieve them. INCLUDE – We foster an open and safe space for all. INTEGRITY – We do what’s right. INVENT – We create straightforward, innovative solutions. AI Tools and Your Interview: We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role. Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process. Diversity & Inclusion: Zensurance celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help. Thank You! We review every application with care to find the best fit for our team. While we may take a little time to get back to you due to the high volume of applications we receive, know that a real human (not a bot!) is reviewing yours. We appreciate your patience and can't wait to learn more about you! 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. 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. 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.

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