SafetyWing

Head of Legal

Remote, United States remote Entry Salary not listed
remote Technology & IT Curated
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About the role

At SafetyWing (YC W18), 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.
🌎 About this Role
As our Head of Legal, 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.
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.

👩‍💻 Your responsibilities will include:
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

🧪 We are looking for someone who has
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
😀 We like to work with people who:
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.

🧘 What we offer
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
🚀 We look forward to hearing from you!

Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Role
Technology & IT Operations Project Management Remote Collaboration Sales Writing remote

Likely questions

  1. Tell us about work you have done that is close to the Head of Legal role.
  2. How would you approach your first 30 days at SafetyWing?
  3. Which of Operations, Project Management and Remote Collaboration have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you stay organised and communicate clearly when working remotely?

Prepare before the call

  • A recent example that proves your experience with Operations, Project Management and Remote Collaboration.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Head of Legal role because I can bring practical experience in Operations, Project Management and Remote Collaboration, learn the team quickly, and contribute to the outcomes SafetyWing needs from this hire.

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