Location: While this position is posted in a specific location, all of Oyster’s positions are fully remote and you can work from home. Forever. To create the best experience for our new hire, this role requires at least 3-4 hours of overlap with Central European Time (CET/CEST) business hours to support collaboration with the team.

Role Summary

Oyster is looking for a sharp, self-driven Senior Employment Counsel to contribute to Oyster's growth and shape the future of global distributed work. As part of our Employment Law Team, you'll advise internal teams and external stakeholders on employment law matters across multiple jurisdictions, playing a direct role in how Oyster supports workers and companies around the world.

A core part of the role is researching and staying current on employment laws and regulations across jurisdictions; managing employment templates, policies, and standard employment processes; liaising with outside counsel on local legal requirements; creating clear, accessible guidance on hiring, managing, and terminating workers globally; and advising Oyster's Platform and Product teams on building a scalable, compliant technology platform. You'll also contribute to the strategic development of our employment-as-a-platform model.

Because Oyster operates as an Employer of Record (EOR), a solid understanding of how that model works, and the unique legal considerations it creates for Oyster, our customers, and their team members, is essential to this role.

The right candidate brings extensive employment law experience, including multi-jurisdictional and cross-border matters, and a track record of advising HR and business partners. Knowledge of immigration rules and employee benefits is a plus. Beyond legal expertise, we're looking for someone who translates complex issues into clear, practical guidance for non-legal audiences, balancing compliance with pragmatic problem-solving, anticipating emerging risks, and partnering strategically with the business to deliver outcomes that are both legally sound and operationally effective.

We also value candidates who embrace AI and other technology tools to enhance efficiency, streamline workflows, and scale the impact of their legal expertise.

Key Responsibilities

• Own and maintain employment templates, policies, and processes across multiple jurisdictions, ensuring Oyster's employment offering remains compliant, scalable, and operationally effective.
• Monitor legislative and regulatory developments globally, assess their impact on Oyster's products and operations, and drive implementation of required changes.
• Partner closely with Product, People team and other cross-functional stakeholders to design and implement compliant employment solutions that balance legal requirements with business objectives.
• Advise on a broad range of employment law and compliance matters across the employee lifecycle, including hiring, compensation, leave, performance management, terminations.
• Support strategic initiatives such as Direct Expansion, indirect-to-direct migrations, and the launch of new employment products and features.
• Research complex employment law issues and translate legal analysis into clear, practical, and business-focused recommendations.
• Develop and maintain employment guides, knowledge resources, and compliance documentation to support scalable operations across Oyster's global footprint.
• Support labor inspections, audits, regulatory inquiries, and other employment compliance initiatives.
• Use data, stakeholder feedback, and operational insights to identify risks, improve processes, and enhance the effectiveness of Oyster's employment compliance framework.
• Identify and champion opportunities to leverage AI, automation, and process innovation to improve team efficiency, reduce manual work, and enable the scalable delivery of employment compliance and legal support.
• Contribute to a highly collaborative, remote-first team culture and help drive continuous improvement across Employment Products.

Core Requirements

• Law Degree (e.g. JD or equivalent) and admission to practice law in one or more jurisdictions.
• 4+ years of experience practicing employment law, preferably with a combination of law firm and in-house practice.
• Deep expertise in employment law, including hands-on experience with standard employment processes: drafting and reviewing contracts, managing templates and policies, advising across a wide range of employment matters and interpreting local labor regulations across multiple jurisdictions.
• Understanding of the EOR model and ability to anticipate and navigate its unique legal challenges; prior experience working with or within an EOR is preferred.
• Experience managing multi-jurisdictional and/or cross-border employment matters, with the ability to work across diverse legal systems and regulatory environments.
• Strong business acumen with the ability to distill complex legal concepts into clear, practical, and actionable guidance for non-legal stakeholders; creativity and pragmatism in risk mitigation are essential.
• Excellent analytical, communication, and research skills, with a keen eye for detail and the ability to manage multiple priorities in a fast-paced, global environment.
• A technology-forward mindset, including curiosity and comfort with leveraging AI and automation tools to work more efficiently and continuously improve legal processes.
• A positive attitude and willingness to assist others, no matter how small the task.

You'll also need

• A reliable home internet connection.
• Fluency in both written and spoken English.