Jobs in Cheltenham, United Kingdom

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 within the EMEA region

Oyster is hiring a Director & Senior Managing Counsel (Employment Law) to lead our Claims & Escalations team and help shape how we support a global, distributed workforce. This role reports directly to our General Counsel and plays a key part in guiding the company through complex employment‑law issues across multiple countries.

The core of this job is deep, hands‑on employment law expertise. We’re looking for someone who brings significant experience advising on employment matters, ideally across several jurisdictions or in cross‑border contexts. This includes partnering closely with HR, drafting and reviewing policies and employment agreements, and managing litigation or contentious matters. If you enjoy being the go‑to person for tough employment‑law calls, this is the kind of role where you’ll have real impact.

You’ll manage a team of attorneys and legal professionals who support both internal partners and external clients. Together, you’ll work with outside counsel, research local laws and regulations, and guide our People Advisory and People Experience teams through the full employment lifecycle for Oyster’s Staff and Team Members around the world. The team also oversees all employment‑related and commercial claims.

Experience with immigration rules, employee benefits, or global workforce issues is a plus.

There’s also space for broader legal work, such as corporate diligence, contract drafting and negotiation, and developing company‑wide policies and procedures, so you’ll touch a wide range of topics while still anchoring the function in solid employment‑law leadership.

We are looking for someone bright, energetic, and a self‑starter. The successful candidate will be an employment lawyer able to handle any responsibility assigned, who can successfully work on their own but is also not afraid to ask for help.

• Successfully manage a team of remote lawyers and legal specialists located around the world
• Advise on Employment law issues, including escalations arising from customer and team member engagements, and the complexities of balancing Oyster’s legal obligations with customer expectations
• Oversee all claims and disputes, liaising with outside counsel
• Provide advice and counsel to internal stakeholders at all levels of the organization, and external stakeholders as required, regarding employment law and employment‑related issues in various countries
• Work cross‑functionally with Oyster’s People Services, Operations, and Revenue teams to support the entire employment lifecycle of Oyster’s internal colleagues and external team members
• Liaise with and manage outside counsel, to include managing and monitoring legal spend and outside counsel performance
• Collaborate with other Legal Teams to solve complex legal issues, create efficiencies and support department‑wide initiatives
• Other duties as assigned

• At least 7+ years PQE practicing employment law
• Juris Doctorate or other qualified lawyer admitted to practice in one or more jurisdictions
• “In‑house” experience working within a corporate legal department
• Law firm experience, including in the practice of litigation
• People management experience
• Experience working in a remote work environment
• Experience advising on employment law compliance in one or more APAC, LATAM or European countries
• Experience with drafting employment and non‑compete agreements, and handling employment terminations, transfers and employee complaints
• Ability to handle complex legal issues involving various countries laws (including employment‑related questions and global workforce issues)
• Capable of explaining complex legal theory, terminology, and issues in easy‑to‑understand language for digestion by Oyster Team Members, Staff, and Customer Companies
• Excellent analytical, communication, and research skills
• 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
• Experience in one or more of the following areas would be beneficial:
• Working at an EOR or PEO
• Advising on employee benefits (retirement and welfare plans, equity or stock options, or executive compensation)
• Advising a multinational organization on cross‑border compliance issues
• Immigration law or global mobility experience
• Experience with corporate due diligence
• Experience with employee benefits

• A reliable home internet connection (or be able to get one)
• Fluent English language skills – both written and spoken