Founding Enterprise Account Executive

About the Role

Build and own the enterprise sales motion for an AI-powered insurance technology startup. As an early sales team member, you will partner with the CEO to take enterprise opportunities from initial outreach through close and help establish the go-to-market playbook.

What You'll Do

• Build and manage an outbound-led pipeline, from prospecting and discovery through product demonstrations and closing.

• Develop the sales playbook and processes that support the company's growth.

• Work with the CEO across the full sales cycle, managing enterprise opportunities and deal progression.

• Identify opportunities to expand customer relationships and product adoption.

• Navigate complex, multi-stakeholder sales with technical buyers and business leaders at insurance carriers.

What We're Looking For

• Three to eight years of relevant experience, including at least one year closing enterprise deals.

• Experience selling AI, data, SaaS, or other highly technical products to technical buyers.

• A track record of building and owning an outbound sales pipeline end to end.

• Ability to navigate multi-stakeholder sales and communicate effectively with technical and business audiences.

• Comfort working in an early-stage environment and building sales processes from the ground up.

Compensation & Benefits

Annual salary range: $125,000 to $170,000 USD. Visa sponsorship is available.

Location

Remote within the United States, with Chicago as the primary location.