Overview
We are partnering with a well-established insurtech leadership team launching a new AI-native software company focused on transforming the employee benefits industry. Backed by founders with more than 20 years of industry experience and a successful technology business serving the insurance market, this startup is rebuilding the employee benefits workflow from the ground up using AI. The company is seeking its first sales hire to help bring its platform to market, secure design partners, and acquire its first customers. This is a true founding commercial opportunity with significant influence over the company's go-to-market strategy.
The Opportunity
● Join as the first commercial hire in the United States
● Build the company's go-to-market motion from the ground up
● Leverage your existing network within the employee benefits ecosystem
● Help secure early design partners and the company's first customers
● Work directly with experienced founders who have built successful insurance technology
businesses
● Play a foundational role in shaping the future sales organization
Key Responsibilities
● Generate new business through existing relationships and strategic prospecting
● Build and execute the company's initial sales strategy
● Identify and engage employee benefits brokers across the U.S.
● Secure design partners and early adopter customers
● Conduct product demonstrations and manage the full sales cycle
● Gather customer feedback and help influence product development
● Develop repeatable sales processes and best practices
● Serve as a trusted advisor to brokers evaluating AI solutions
● Collaborate directly with the founders on product positioning and market strategy
Required Experience
● Proven success selling B2B SaaS or technology solutions
● OR prior experience as an Employee Benefits Broker with a strong industry network
● Existing relationships within the employee benefits brokerage community
● Demonstrated ability to build pipeline and close new business
● Strong consultative selling and relationship-building skills
● Experience working in startup or high-growth environments preferred
● Entrepreneurial mindset with a desire to build something from the ground up
Preferred Background
● Former Employee Benefits Broker looking to transition into technology sales
● Experience selling solutions into employee benefits brokers or agencies
● Experience with platforms such as Employee Navigator, Ease, or similar employee
benefits technology
● Understanding of employee benefits administration, enrollment, quoting, or proposal
workflows
● Experience helping launch new products or entering new markets
● Leadership potential to help build a future sales organization
Ideal Profile
● Well-connected within the employee benefits industry
● Builder mentality with strong entrepreneurial drive
● Comfortable wearing multiple hats in an early-stage startup
● Highly self-motivated with excellent communication skills
● Passionate about AI and modernizing legacy industries
● Excited to help acquire the company's first 10 to 20 customers
Why This Role
● Founding sales hire with significant ownership and influence
● Opportunity to help define the company's go-to-market strategy
● Experienced founding team with proven success in insurtech
● AI-native platform solving meaningful workflow challenges
● Ability to shape both the product and commercial organization from day one
● Strong long-term growth opportunity as the company scales
Pay: $130,000.00 - $140,000.00 per year
Work Location: Remote
