Senior Counsel (Claims & Escalations)

Right now, the best jobs are limited to people in a handful of the world’s wealthiest cities, yet brilliant people are everywhere. Driven to overturn the status quo and distribute opportunities equally around the world, Oyster launched its global employment platform to help companies hire, pay, and care for talent anywhere.

When it comes to global employment, we walk the walk. We’re proof that companies don't need an office to create a highly-engaged culture. Since the company’s inception in January 2020, Oyster has:

🌏 Created a fully-distributed, vibrant team of 400+ employees across 60+ countries

👩‍💻Featured in Forbes having ranked #9 in Flexjobs Top 30 Companies for remote jobs

🌈 Established a diverse leadership team and an employee base that’s 60% female

🏆 Achieved one of the highest employee engagement scores in its class

🦄 Raised $286 million to date, with a current valuation of $1.2 billion!

💚 B Corp status achieved in 2023

Our momentum speaks to the power of global employment—and we’re just getting started! If you want to change the world with Oyster and be empowered to work remotely while doing so, we’d love for you to apply!

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 you to be based in the United States, in Eastern or Central Time Zones (UTC -5/-6).

Oyster is looking for an Employment Counsel to contribute to Oyster's growth to become the world leader in global distributed working. This role will be a part of our Employment Law Team and will focus on providing advice and counsel to internal and external stakeholders regarding employment law and employment-related issues around the world. A core part of the role is managing employment-related claims and risk. You and your teammates will liaise with outside counsel and research legal issues to understand local employment laws and regulations; create easy-to-digest collateral around employing workers in various countries; support the People Services team in managing the full lifecycle of employment; and advise on the strategic management and growth of our employment as a platform product.

Additionally, because Oyster operates as an Employer of Record (EOR), this role also requires a solid understanding of how the EOR model functions and the unique legal considerations it creates for Oyster, our customers, and the team members engaged with our customers.. Assisting with immigration issues may also be required.

Oyster needs someone with extensive knowledge and experience in Employment Law, with deep expertise in United States employment law. Experience managing multi-jurisdictional and cross-border employment issues, and advising and supporting HR and business partners, is also required. Canadian employment law expertise is a strong bonus. Helpful but not required is knowledge of immigration rules and employee benefits.

Success in this role requires strong business acumen and the ability to translate complex, cross-border employment law issues into clear, practical guidance for non-legal stakeholders. The right candidate balances compliance considerations with pragmatic problem-solving and brings creativity to risk mitigation rather than relying on purely technical answers. At this level, we are seeking someone who not only provides sound legal advice, but also demonstrates strong business acumen—integrating practical, solution-oriented guidance into their legal risk analyses. This person anticipates emerging risks, keeps scalability front of mind, and partners strategically with the business to drive outcomes that are both legally compliant and operationally effective.

Additional responsibilities may include corporate diligence support, contract creation, negotiation and execution, and developing organizational policies and procedures. Because of Oyster’s global and fast-paced environment, you will likely touch many facets of law.

We are looking for someone bright, energetic, and a self-starter. The successful candidate will be able to handle any responsibility assigned, and can successfully work on their own, but is also not afraid to ask for help. Responsibility may include:

• Providing advice and counsel to internal stakeholders regarding employment law and employment-related issues in various countries, with emphasis on the United States

• Advising on issues unique to the EOR model, including escalations arising from customer and team member engagements, and the complexities of balancing Oyster’s legal obligations with customer expectations

• Researching issues and advising internal colleagues

• Liaising with outside counsel as necessary

• Creating accessible resources that break down complex global employment matters into simple and actionable guidance.

• Managing employment-related claims and risk

• Conducting training for internal partners on both substantive employment law issues and internal processes

• Partnering with customer-facing teams and supporting them through drafting and ghostwriting customer-and team member-facing communications

• Other duties as assigned
  

• Juris Doctorate and admission to practice law in at least one U.S. jurisdiction

• At least 5+ years’ experience practicing U.S. employment law, preferably with a combination of law firm and in-house experience

• Fluent English language skills

• Deep expertise in U.S. employment law, including extensive experience analyzing exempt vs. non-exempt classifications under the Fair Labor Standards Act (FLSA) and state-level equivalents

• Experience managing multi-jurisdictional and cross-border employment issues, and advising and supporting HR business partners

• Understanding of the EOR model and ability to anticipate and navigate its unique legal challenges

• Canadian employment law expertise is a strong plus (as is additional country experience)

• Experience with drafting employment and non-compete agreements, and handling employment terminations, transfers, employee complaints, and claims

• Ability to handle complex legal issues involving various countries’ laws (including employment-related questions and global workforce issues)

• 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

• Demonstrated ability to partner directly with leadership and business stakeholders, influence decision-making, and contribute to strategy

• A positive attitude and willingness to assist others, no matter how small the task

• Ability to work in a fast-paced, high-output, team-oriented, practical environment

• A reliable home internet connection (or be able to get one)

• Fluent English language skills

Our values guide the work we do, the decisions we make, and the culture that makes us special. We elevate talent. 🙌  We build trust. 🤝 We thrive together. 🌍

Our mission is to create a more equal world—one global hire at a time. Everything we do ladders up to our mission—and that doesn’t just mean building software. We develop programs, participate in workshops, and create dedicated teams to ensure we successfully support companies and knowledge workers in this new world of work. 

We embrace asynchronous communication and collaborative work—and we share how we work in the Oyster Public HQ —to help other global teams learn from our experiences.

Different countries have different statutory benefits, different cultures have different norms, and different people have different needs! In order to best support and encourage our diverse team, we’ve created How YOU Work; a program of policies, practices, and perks to support your whole human experience as an employee at Oyster.

• Work from anywhere: Oyster is a borderless, HQ-less company. As long as your work gets done on time, your team has the support they need, and you're authorized to work where you live, the world is truly your Oyster.

• Paid time off: We’re all about taking breaks—we all need it. Oyster provides employees with 40 days off each year, which includes public/bank holidays and vacation/holiday leave (unless your country mandates more).

• Mental health support: We consider your mental health a top priority. We offer access to Plumm, a mental well-being service, to support your mental health.

• Wellbeing allowance:  Each month, Oyster will top up your ThanksBen wallet with a wellbeing allowance. You can get pretty much anything that your heart desires! ThanksBen offers a wide array of options for spending your wellbeing allowance. Check out their benefits catalogue here for inspiration.

• Flexible parental leave: Families are created in lots of different ways. Our parental leave policy applies to all employees who are becoming parents, regardless of how they become a parent. Oysters are eligible for a minimum of three months of paid parental leave and your job will be held for 12 months (or longer if required by local jurisdiction).

• WFH stipend: Stipend to spend on your laptop and any other equipment you need for your home office; we'll get you up and running in no time!

At Oyster, we celebrate a variety of perspectives and experiences and we’ve intentionally built our product and our company with an inclusive, global mindset. We know from experience that people from underrepresented groups often don’t apply for roles they don’t feel they meet all the criteria for. We’re committed to elevating talent by creating a trust-based environment where we can all thrive together. So if you think you have what it takes, but don’t necessarily check every single box, please consider applying. We’d love to hear how you might contribute to our mission and our team.

Oyster is committed to ensuring equal opportunity of employment for qualified persons with disabilities and actively fosters an inclusive work environment. If you require reasonable accommodations throughout the recruiting process, please email [email protected] with the subject line: Interview Accommodations.

Our available positions are published on our careers page and should you be invited to interview with us, our recruitment team will only ever contact you directly from an @oysterhr.com email address. We will never ask you to send us money as part of a job offer. If you receive a suspicious email relating to opportunities at Oyster from any other email domain where someone is claiming to be a part of our recruitment team, or are directed to anywhere other than www.oysterhr.com/careers to view our available jobs we encourage you to submit a report through our Compliance and Ethics Helpline.