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.