Enterprise Account Executive

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

Enterprise Account Executive | AI Startup

SF/NYC hybrid 2–3 days/week | Chicago remote

Early-stage, venture-backed AI startup

A fast-growing AI startup is hiring two Enterprise Account Executives to help build its enterprise sales motion from the ground up.

The company is building an AI Analyst for Insurance P&L Teams, helping insurance and actuarial teams automate data-heavy compliance, pricing, regulatory, and analytical work.

Founded in 2025, the startup has raised $10M from leading venture capital firms and is already seeing strong traction:

• 80% of POCs convert to paying customers
• Customers expanding to 400+ users within months
• 17-person team
• $6T+ insurance market

This is a true founding sales role. You’ll help build the playbook, create pipeline, and shape the enterprise sales motion future AEs will follow.

What you’ll do

• 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

Approximately 85% of pipeline generation is outbound, and typical sales cycles are 30–60 days.

What we’re looking for

• 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, ideally 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
• Bachelor’s degree or equivalent experience
• Genuine enthusiasm for startups and building from scratch

Experience selling AI, data, developer tools, infrastructure, or technical SaaS is especially valuable. Insurance experience is not required.

What success looks like

We value measurable performance, including:

• Largest deals closed and ACV
• Quota and attainment
• Self-generated pipeline
• Outbound opportunities created
• Promotions or top-performer recognition

This role is ideal for someone who enjoys ambiguity, moves quickly, asks thoughtful questions, and wants to build rather than inherit.

Compensation and location

OTE: $230K–$340K

Structure: Approximately 50/50

Equity: Competitive

San Francisco: Preferred, hybrid 2–3 days/week

New York: Hybrid 2–3 days/week

Chicago: Remote available

Visa transfers may be considered, including OPT and H-1B transfers.

If you’ve closed complex enterprise technology deals, know how to build your own pipeline, and want to help create an enterprise sales organization from the ground up, we’d love to hear from you.