About SafetyWing:
SafetyWing is on a mission to build the first global social safety net — health, insurance, and retirement products that support remote workers, digital nomads, and globally distributed teams. We believe freedom shouldn’t be limited by geography, and we’re creating tools that make global living safer and more sustainable.
Our flagship product, Remote Health, is an international health insurance plan covering people in over 175 countries. It moves with you, whether you work from home, travel full-time, or run a remote-first business.
Role Overview:
We’re hiring a Head of Agent Sales to design and lead a brand-new global sales network of commission-only insurance agents. This is not a typical sales role — it’s entrepreneurial, high-risk, and high-reward. Your earnings will be tied directly to the performance of the agent network you build.
You’ll launch this program from scratch, build systems, recruit agents, and motivate them to succeed. With your leadership, the goal is to scale the network to over 1,000 active agents within two years.
Key Responsibilities:
- Build and lead a global network of commission-only sales agents for Remote Health
- Design systems, processes, and playbooks for scalable agent recruitment and performance
- Recruit, onboard, and train licensed insurance brokers from around the world
- Provide ongoing coaching and motivation to hit ambitious global sales goals
- Utilize top-tier tools (HubSpot, Apollo, Gong) to support efficient agent operations
- Work closely with legal, HR, and operational teams to keep your focus on sales
- Uphold and promote SafetyWing’s values and customer-first philosophy throughout the network
What We’re Looking For:
- Experience in B2B insurance sales, especially international or remote health
- Proven success in recruiting and managing licensed insurance brokers
- Entrepreneurial mindset — you enjoy building from zero and thrive in fast-paced, unstructured environments
- Resourceful and self-directed with the ability to create systems and grow a team independently
- Excited by the opportunity to help shape a global sales operation with real impact
- Personally aligned with SafetyWing’s mission to create equal opportunity worldwide
You’ll Fit Right In If You:
- Think independently and creatively
- Are bold enough to try new ideas, even if they fail
- Take ownership of your work and lead with integrity
- Enjoy working with curious, mission-driven people
- Are motivated by long-term impact rather than just short-term gains
What We Offer:
- 100% remote position — work from anywhere in the world
- Commission-only role with no cap on earning potential
- Operational support and access to industry-leading tools
- A chance to build a global sales organization from the ground up
- Work with a remote-first team spread across ten time zones
- Join a company backed by Y Combinator (W18), with global vision and strong momentum
