Founding Enterprise Account Executive

About the Role

Join an early-stage AI platform team as its founding enterprise seller. You will build the enterprise sales motion from the ground up and work closely with company leadership to close complex deals with large insurance organizations.

What You'll Do

• Build and manage your pipeline end to end, with a strong focus on outbound prospecting, discovery, product demonstrations, and closing.

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

• Own the full sales cycle, from initial conversations through close, for enterprise deals typically valued at $200,000 or more.

• Partner with customers to drive account expansion after the initial sale.

• Navigate multi-stakeholder sales involving technical buyers, product leaders, and business owners at large insurance organizations.

What We're Looking For

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

• Experience building outbound pipeline, including prior SDR or BDR work.

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

• Comfort creating sales processes from scratch and working without the established playbooks or extensive sales support of a large organization.

• A bachelor's degree or equivalent, enthusiasm for startups, and a consistent employment history.

• Experience in technology sectors beyond retail, transportation, or automotive.

Compensation & Benefits

Base salary is $125,000 to $170,000 annually. Visa sponsorship is available. Equity details were not provided.

Location

Remote, with Chicago as the primary location. Candidates may also be based in San Francisco or New York.