Founding Enterprise Account Executive

True Talent Solutions Partners; United States; Remote; USD 125,000 - 170,000; Full time

Job summary

True Talent Solutions Partners in the United States is seeking a Founding Enterprise Account Executive to own the enterprise sales motion for a B2B AI insurance platform. You will work with company leadership to shape the sales playbook and drive deals with insurance buyers.

You will build and manage an end-to-end pipeline, lead the full sales cycle, and identify expansion opportunities to increase platform adoption.

Qualifications

• 3–8 years of experience closing B2B SaaS deals at startups.
• Experience closing enterprise deals with $200,000+ annual contract value.
• Experience building outbound pipeline (SDR/BDR role).
• Experience selling AI, data, or other highly technical products to technical buyers.
• Bachelor's degree or equivalent; thrives in startup environments.

Responsibilities

• Build and manage an enterprise pipeline end to end.
• Develop the sales playbook and processes for go-to-market growth.
• Lead full sales cycle from initial conversations through contract close (30–60 days).
• Support customer expansion by growing platform adoption.
• Navigate multi-stakeholder sales with technical and business decision-makers at insurance companies.

Skills

SaaS sales

Enterprise closing

Outbound prospecting

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.