Senior Product Manager owning payments, ledgering and banking infrastructure. Building Float’s financial operating system for Canadian businesses.
About the role
- Lead Product Manager at Oyster managing product vision and execution across Hire & Onboard or Benefits domains. Collaborating with cross-functional teams to drive successful outcomes in a remote-first environment.
Responsibilities
- Own the product vision and strategy for either the Hire & Onboard or Benefits domain, aligned with company goals and customer outcomes.
- Lead discovery and prioritisation across hiring and onboarding problems, balancing new features, regulatory needs, tech debt, and operational improvements.
- Translate strategy into execution, defining clear roadmaps, outcomes, and success metrics.
- Partner closely with Engineering and Design to deliver high-quality, scalable solutions with strong user experience.
- Collaborate with cross-functional stakeholders including Operations, Legal/Compliance, and Go-to-Market to ensure feasibility and alignment.
- Represent the Hire & Onboard or Benefits domain in senior stakeholder forums, clearly communicating trade-offs, progress, risks, and impact.
- Identify and evaluate opportunities to leverage AI and automation to improve hiring and onboarding outcomes, efficiency, and decision-making.
- Use data and insights (quantitative and qualitative) to inform decisions, measure impact, and continuously improve outcomes.
- Ensure regulatory and compliance requirements are embedded into product development without compromising usability or speed.
- Continuously improve product processes, contributing to best practices across the wider Product organisation.
Requirements
- 5+ years of experience in Product Management, with a strong track record of owning complex product areas end-to-end and driving measurable business and customer outcomes.
- 3+ years of experience in HR tech, hiring, onboarding, benefits, payroll, compliance, or B2B SaaS, with a solid understanding of regulated or operationally complex domains.
- Strong product discovery and problem-framing skills, with the ability to deeply understand customer pain points, validate assumptions, and translate insights into impactful product solutions.
- Hands-on experience building or iterating on AI-powered and automation-driven features, including defining use cases, evaluating trade-offs, and measuring real-world impact.
- Highly data-driven, comfortable using qualitative and quantitative insights to inform prioritisation, measure success, and continuously improve outcomes.
- Experience working in multinational, cross-functional environments, collaborating effectively across Engineering, Design, Legal, Compliance, Operations, and Go-To-Market teams.
- Comfortable operating in ambiguity, with a proactive, ownership-driven mindset and the ability to bring clarity and structure to complex or evolving problem spaces.
- Strong standards for quality, ethics, and transparency, particularly when building products that impact people, employment, and compliance.
- Proven experience in scale-up or high-growth environments, with the ability to balance speed, quality, and long-term sustainability.
- A reliable home internet connection (or be able to get one).
- Fluent English language skills.
Benefits
- 40 days off per year (including holidays and vacation), or more if required by your country.
- Access Plumm, our mental well-being service.
- Each month, receive a wellbeing allowance in your ThanksBen wallet.
- All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months or as required locally.
- Receive a stipend for your laptop and home office equipment to get you set up quickly.
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