Founding Enterprise Account Executive

ABOUT THE ROLE Join an early-stage AI and B2B SaaS team to build its enterprise sales motion from the ground up. You will partner closely with company leadership to sell a technical platform to large insurance organizations and shape how the business grows. WHAT YOU'LL DO - Build and manage an enterprise pipeline end to end, from outbound prospecting and discovery through demos, negotiation, and close. - Develop the sales playbook and processes as an early member of the sales team. - Own the full sales lifecycle, partnering with leadership on complex deals and typical 30-to-60-day sales cycles. - Drive customer expansion and adoption after the initial sale. - Navigate multi-stakeholder sales with technical buyers and business decision-makers at large insurance carriers. 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. - Ability to sell AI, data, or other highly technical products to technical buyers. - Experience working outside large organizations with established sales playbooks and extensive SDR support. - A bachelor's degree or equivalent, enthusiasm for startups, and a record of sustained tenure in recent roles. - Technology industry experience beyond retail, transportation, or automotive. COMPENSATION & BENEFITS Base salary is $125,000 to $170,000 USD annually. Visa sponsorship is available. LOCATION Remote within the United States, with Chicago as the primary location. The role is also open to candidates in San Francisco and New York.