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. #J-18808-Ljbffr True Talent Solutions Partners