Founding Enterprise AE — Build AI Sales From Scratch Remote

Jack; New York (NY); Hybrid; USD 230,000 - 340,000; Full time

Benefits offered by this job

Equity

Hybrid work

Remote option (Chicago)

Job summary

Jack, an early-stage AI startup, is hiring two Enterprise Account Executives to build its enterprise sales motion from the ground up. The role is NYC/ SF hybrid 2–3 days per week with Chicago remote as an option. You will own outbound pipeline, run discovery and demos, and close enterprise deals of $200K+ ACV.

You will shape the playbook, create pipeline, and drive GTM strategy, partnering closely with the CEO. Equity and an OTE of $230K–$340K are included.

Qualifications

• 3–8 years of B2B SaaS closing experience, ideally at startups.
• At least 1 year closing $200K+ ACV enterprise deals.
• Experience at a high-growth startup, Series C or earlier.
• Proven ability to build outbound pipeline independently.
• Strong track record of quota attainment.
• Experience owning net-new business from prospecting through close.
• Comfort operating without an established sales playbook.
• Genuine enthusiasm for startups and building from scratch.

Responsibilities

• Build outbound pipeline from scratch.
• Run discovery, demos, and technical sales conversations.
• Manage complex, multi-stakeholder sales cycles.
• Close enterprise deals of $200K+ ACV.
• Own opportunities from first conversation through signature.
• Partner directly with the CEO.
• Help develop sales messaging, processes, and GTM strategy.
• Drive expansion within existing customers.

Skills

Outbound pipeline

Discovery & demos

Complex multi-stakeholder sales

Closing large deals

Startup environment

Quota attainment

Prospecting from scratch

Executive engagement

Education

Bachelor's degree or equivalent

Job description

Jack, an early-stage AI startup, is hiring two Enterprise Account Executives to build its enterprise sales motion from the ground up. The role is NYC/ SF hybrid 2–3 days per week with Chicago remote as an option. You will own outbound pipeline, run discovery and demos, and close enterprise deals of $200K+ ACV.

You will shape the playbook, create pipeline, and drive GTM strategy, partnering closely with the CEO. Equity and an OTE of $230K–$340K are included.