Overview

SafetyWing (YC W18) is seeking a Head of Agent Sales to create and lead a new global network of commission-only agents from the ground up. This is not an ordinary sales leadership role – it’s entrepreneurial, high-risk, and high-reward. You’ll be paid a commission on all sales made in your network, meaning success could lead to substantial income.
This role is focused on Remote Health – a global health insurance plan that works in over 175+ countries and follows you wherever you go. It is used by globally distributed teams and businesses that operate remotely.
At SafetyWing, 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.

Your responsibilities will include

  • Designing and launching a global, commission-only agent sales organization for Remote Health
  • Recruiting, onboarding, and motivating agents to achieve ambitious sales goals
  • Building scalable systems, processes, and playbooks for rapid growth – targeting 1,000 active agents within two years
  • Leveraging our tools (HubSpot, Apollo, Gong) and legal/HR resources to keep your focus entirely on sales
  • Upholding SafetyWing’s values and ensuring agents are trained to do the same

We are looking for someone who

  • Has experience in B2B insurance sales, with a strong understanding of broker networks
  • Knows how to recruit, onboard, and motivate licensed insurance brokers
  • Is highly autonomous and thrives in entrepreneurial, build-from-scratch environments
  • Brings an existing network or the resourcefulness to build one quickly
  • Is energized by our mission to create a global social safety net-and wants to play a key role in bringing it to life
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
  • Commission-only structure with uncapped earning potential (high reward for success)
  • Access to top-tier sales tools and operational support, so you can focus on building sales
  • The opportunity to scale a global sales organization and leave a lasting impact
We look forward to hearing from you!

About SafetyWing

SafetyWing was founded to support nomads like ourselves by building an adaptable software-based global social safety net.
Our products are created by a fully remote team distributed across the globe and stretching ten timezones while headquartered in San Francisco.
We’re here to remove the role of geographical borders as a barrier to equal opportunities and freedom for everyone.