Enterprise Account Executive

Enterprise Account Executive | AI Startup

📍 San Francisco preferred | New York | Chicago

💰 $125K–$170K base | $230K–$340K OTE + equity

🏢 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
• 100% win rate against legacy competitors in head-to-head deals
• Enterprise deals exceeding $200K
• 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
• Prospect into large enterprise accounts
• 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

Strong results matter more than recognizable logos on a résumé.

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

Compensation and location

Base salary: $125K–$170K

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.