Founding Enterprise AE: AI Insurance SaaS (Remote)

True Talent Solutions Partners

Chicago (IL)

Remote

USD 125,000 - 170,000

Full time

3 days ago

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Job summary

True Talent Solutions Partners is seeking a Founding Enterprise Account Executive to own and drive the enterprise sales motion for a B2B AI insurance tech platform. You will shape the sales playbook and lead deals from discovery to close, engaging with insurance buyers and leadership.

You will build outbound pipelines, demonstrate the platform, and navigate multi-stakeholder decisions in a startup environment. This fully remote role offers a strong compensation package and sponsorship options.

Qualifications

3–8 years closing B2B SaaS deals
At least 1 year closing enterprise deals with $200,000+ ACV
Experience building outbound pipeline
Experience selling AI or highly technical products to technical buyers
Bachelor's degree or equivalent; enthusiasm for startup environments; experience working outside large organizations
Experience in technology industries with tenure in recent roles

Responsibilities

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.