Founding Enterprise Account Executive

About the Role

Join an early-stage enterprise AI software startup as its Founding Enterprise Account Executive. You will build the sales motion from the ground up, working closely with the CEO to bring a technical AI platform to large organizations, including insurance carriers.

What You'll Do

• Build and manage an enterprise pipeline, from outbound prospecting and discovery through demos, negotiation, and close.

• Develop the sales playbook and processes that support the company's go-to-market growth.

• Partner with the CEO across the sales cycle and take ownership of opportunities from first conversation through close.

• Lead complex deals with multiple stakeholders, including technical buyers, product leaders, and business owners.

• Support customer expansion by identifying opportunities to broaden platform adoption.

What We're Looking For

• Three to eight years of experience closing B2B SaaS deals at startups, including at least one year closing enterprise contracts with $200K+ in annual contract value.

• Experience building outbound pipeline, including prior SDR or BDR work, and managing enterprise opportunities independently.

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

• Enthusiasm for startup environments, comfort building processes from scratch, and a bachelor's degree or equivalent experience.

• Familiarity with complex buyers and industries such as insurance is useful.

Compensation & Benefits

Annual salary range: $125,000 to $170,000 USD. Visa sponsorship is available.

Location

Remote within the United States, with Chicago as the primary location.