Founding Enterprise Account Executive

About the Role

A growing AI platform company is seeking a founding Enterprise Account Executive to build and own its enterprise sales motion. You will partner with company leadership and help bring technical AI solutions to large insurance organizations.

What You'll Do

• Build and manage pipeline end to end, from outbound prospecting and discovery through product demonstrations and closing.

• Develop the sales playbook and processes as an early member of the sales team.

• Partner with the CEO across the full sales cycle, including enterprise deals with typical cycles of 30 to 60 days.

• Drive customer expansion after initial deals close.

• Navigate multi-stakeholder sales with technical and business buyers, including actuaries, product leaders, and P&L owners.

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 from scratch, including prior SDR or BDR experience.

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

• Experience working at high-growth startups and outside large organizations with established sales playbooks and SDR support.

• A bachelor's degree or equivalent, enthusiasm for startups, and a record of staying at least one year in all but at most one recent role.

• Experience in a technology industry beyond retail, transportation, or automotive.

Compensation & Benefits

Base salary range: $125,000 to $170,000 USD 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.