Founding Enterprise Account Executive

ABOUT THE ROLE Join an early-stage AI and machine learning company as its first enterprise sales hire. You will build the sales motion from the ground up and work closely with the CEO to sell a technical AI platform to large insurance carriers. WHAT YOU'LL DO - Build and manage pipeline end to end, with an emphasis on outbound prospecting, discovery, product demos, and closing. - Develop the sales playbook and processes that support the company's go-to-market strategy. - Lead the full sales cycle in partnership with the CEO, from initial conversation through close. - Grow customer relationships and identify opportunities to expand adoption. - Navigate multi-stakeholder sales involving 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 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 highly technical products to technical buyers is valuable. - Comfort working in a high-growth startup environment without relying on an established sales playbook or extensive SDR support. - A bachelor's degree or equivalent, enthusiasm for startups, and a track record of at least one year in most recent roles. - Experience in technology industries beyond retail, transportation, or automotive; consulting experience is not a fit for this role. COMPENSATION & BENEFITS Base salary is $125,000 to $170,000 USD annually. Visa sponsorship is available. LOCATION Remote, with a primary location in Chicago, United States. Candidates based in San Francisco or New York may also be considered for a hybrid schedule.