JobsAccount ExecutiveChicagoFounding Enterprise Account Executive

True Talent Solutions Partners

Posted 3 days ago · Jobs at True Talent Solutions Partners

Founding Enterprise Account Executive

True Talent Solutions Partners · Chicago, Illinois, United States

Full-timeRemote5-10 yrs$125k–$170kVisa sponsorship listed
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In short

The Founding Enterprise Account Executive will build and manage the end-to-end enterprise sales pipeline for AI solutions. They will also develop sales playbooks and partner with leadership to navigate complex, multi-stakeholder deals.

What they're looking for

MUST-HAVE SKILLS

Enterprise salesB2B SaaSOutbound prospectingPipeline managementSales playbook developmentTechnical salesAI solutionsCustomer expansion

ALSO MENTIONED

Enterprise Account ExecutiveAI platformB2B SaaSOutbound prospectingSales pipelineSales playbookEnterprise dealsTechnical buyersActuariesProduct leaders

Candidates must have three to eight years of experience closing B2B SaaS deals, including at least one year of enterprise-level experience with $200,000+ ACV. A bachelor's degree and a background in selling technical products like AI or data are required.

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Questions about this role

Is this True Talent Solutions Partners role remote?
Tagged remote.
What does it pay?
The posting lists $125,000–$170,000 a year.
Does it sponsor visas?
Visa sponsorship listed.
What experience does it ask for?
Listed as 5-10 years.

The posting, in full

A growing AI platform company is seeking a founding Enterprise Account Executive to build and own its enterprise sales motion. You will partner with company leadership and help bring technical AI solutions to large insurance organizations. Build and manage pipeline end to end, from outbound prospecting and discovery through product demonstrations and closing.

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About the Role

A growing AI platform company is seeking a founding Enterprise Account Executive to build and own its enterprise sales motion. You will partner with company leadership and help bring technical AI solutions to large insurance organizations.

What You'll Do

  • Build and manage pipeline end to end, from outbound prospecting and discovery through product demonstrations and closing.
  • Develop the sales playbook and processes as an early member of the sales team.
  • Partner with the CEO across the full sales cycle, including enterprise deals with typical cycles of 30 to 60 days.
  • Drive customer expansion after initial deals close.
  • Navigate multi-stakeholder sales with technical and business buyers, including actuaries, product leaders, and P&L owners.

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 from scratch, including prior SDR or BDR experience.
  • Background selling AI, data, or other highly technical products to technical buyers.
  • Experience working at high-growth startups and outside large organizations with established sales playbooks and SDR support.
  • A bachelor's degree or equivalent, enthusiasm for startups, and a record of staying at least one year in all but at most one recent role.
  • Experience in a technology industry beyond retail, transportation, or automotive.

Compensation & Benefits

Base salary range: $125,000 to $170,000 USD annually. Visa sponsorship is available. Equity details were not provided.

Location

Remote, with Chicago as the primary location. Candidates may also be based in San Francisco or New York.

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We'll keep this job - the posting's full text, even after it closes. Free.

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This listing comes from True Talent Solutions Partners's own careers site. Apply links go to the employer. Last checked 31 Oct 2026.