Head of Agent Sales

Department: Growth

Employment Type: Freelance

Location: Remote

Description

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!