Founding Enterprise Account Executive

About the Role

A B2B AI insurance technology company is looking for a Founding Enterprise Account Executive to build and own its enterprise sales motion. You will work closely with company leadership and help shape the sales playbook while selling a technical AI platform to insurance buyers.

What You'll Do

• Build and manage an enterprise pipeline end to end, including outbound prospecting, discovery, product demonstrations, and closing.

• Develop the sales playbook and processes that support the company's go-to-market growth.

• Lead the full sales cycle, from initial conversations through contract close, with typical deal cycles of 30 to 60 days.

• Support customer expansion by identifying opportunities to grow platform adoption.

• Navigate complex, multi-stakeholder sales with technical and business decision-makers at insurance companies.

What We're Looking For

• Three to eight years of experience closing B2B SaaS deals at startups, including at least one year closing enterprise deals with $200,000 or more in annual contract value.

• Experience building outbound pipeline, including in a prior SDR or BDR role.

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

• A bachelor's degree or equivalent, enthusiasm for startup environments, and experience working outside large organizations with established sales support and playbooks.

• Experience in technology industries and a track record of sustained tenure in recent roles.

Compensation & Benefits

Base salary: $125,000 to $170,000 annually. Visa sponsorship is available.

Location

Remote, with Chicago as the primary location.