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Head of Agent Sales

SafetyWing

SafetyWing

Sales & Business Development
Remote
Posted on Jul 31, 2025
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.
Department
Growth
Employment Type
Freelance
Location
Remote
Workplace type
Fully remote

💻 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.

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