Founding Enterprise Account Executive

True Talent Solutions Partners; Chicago (IL); Remote; USD 125,000 - 170,000; Full time

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.

Skills

Enterprise sales

Outbound prospecting

AI/Technical sales

B2B SaaS

Startup experience

Education

Bachelor's degree

Job description

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.