Head of Legal

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Application Deadline: 24 July 2026

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Department: Operations

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Employment Type: Permanent - Full Time

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Location: Remote

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Reporting To: Jared Schachter

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Description

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At

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SafetyWing (YC W18)

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, we’re building a global social safety net for remote workers - simple health, insurance, and retirement products designed to replace national welfare systems. Our mission is to remove geographical borders as a barrier to equal opportunity and freedom for everyone. If we succeed, we believe this will be one of the most important tasks of our time.

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🌎 About this Role

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As our

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Head of Legal

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, you will own our legal function, working with legislation across multiple countries. This is a builder role - you'll lead complex legal projects from start to finish, do the deep work yourself, and get leverage through strong relationships with external counsel and, over time, a small internal team.

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You'll work closely with our product, sales, and operations teams on all legal matters, with a focus on clear, practical guidance that helps us move fast and make confident decisions. You’ll play a key role in shaping how SafetyWing builds and scales regulated insurance products globally.

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👩‍💻

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Your responsibilities will include:

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• Own and drive legal and regulatory projects across SafetyWing’s products
• Partner with product teams to work through legal and regulatory trade-offs as products grow and expand into new markets
• Help teams operate confidently in regulated environments by turning complex legal and regulatory questions into clear, actionable guidance
• Work hands-on with international regulatory frameworks, including insurance, data privacy, consumer protection, and advertising laws
• Coordinate and manage regulatory filings and submissions
• Support the resolution of material disputes and regulatory issues alongside internal stakeholders and external partners
• Build structure, documentation, and repeatable processes so legal work can scale with the company

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🧪 We are looking for someone who has

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• Is a qualified lawyer with strong commercial judgment and experience working closely with product, operations, or business teams
• Has experience in regulated environments and enjoys getting up to speed on new legal and regulatory areas
• Has strong project management skills and likes owning complex problems end-to-end
• Thinks practically about risk and understands how legal decisions affect product, sales, and growth
• Knows their limits and works well with external counsel to fill the gaps
• Is comfortable with ambiguity, takes initiative, and moves work forward independently
• Brings integrity, resilience, and a solution-oriented mindset

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😀 We like to work with people who:

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• Want to help build a global social safety net on the Internet.
• Think for themselves instead of copying others.
• Are willing to try new things, even with the risk of failure.
• Are intellectually curious and open to new ideas.
• Are creative and bold in the face of any problems.
• Have strong integrity and do the right thing.

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🧘 What we offer

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• Fully remote work environment – work from anywhere globally
• Unlimited time off
• Equity compensation
• Our own Global Safety Net, giving you worldwide health, income, and travel coverage
• Personal development and office budgets
• A new laptop when you need one
• Annual team gathering in amazing locations - our previous meetups were in Iceland, Vietnam and Argentina

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🚀 We look forward to hearing from you!