Oyster®
Lead Product Manager
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One Opportunity, Two Product Domains
Location: While this position is posted in a specific location, all of Oyster's positions are fully remote, you can work from home, forever. To create the best experience for our new hire, this role requires you to be based within UTC +3 to UTC -5.
We're hiring two Lead Product Managers with the same scope, level, and expectations, supporting two different product domains: Hire & Onboard and Benefits.
By applying to this role, you'll be considered for either opportunity. Throughout the interview process, we'll introduce you to both domains, discuss where your experience and interests align best, and determine together which role is the strongest mutual fit.
As a Lead Product Manager
You will own the product vision, strategy, and execution for a critical area of Oyster's platform. Whether focused on Hire & Onboard or Benefits, you'll lead customer-facing experiences, internal tools, and operational workflows that help companies employ talent globally with confidence, compliance, and simplicity.
You are an AI-first product thinker, comfortable applying automation and AI to solve meaningful customer and operational challenges. You bring strong product judgment, a structured approach to problem-solving, and the ability to balance user needs, regulatory complexity, and business outcomes.
In this role, you'll operate at the intersection of product strategy, execution, and cross-functional leadership. You'll drive complex initiatives in partnership with Engineering, Design, Legal, Compliance, Finance, Operations, and Go-to-Market teams. Strong ownership, clear communication, and the ability to build alignment across diverse stakeholders are essential to success.
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Key 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 prioritization 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 organization.
Core 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 prioritization, 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.
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- A reliable home internet connection (or be able to get one)
- Fluent English language skills
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