Enterprise Account Executive

About the job

An early-stage AI company is automating the insurance industry's most tedious paperwork: organizing documents, reading policies and loss runs, and catching issues that would take hours to find manually. Reporting to the CEO, you will own the full enterprise sales cycle, from executive prospecting and multi-stakeholder discovery through tailored demos, procurement and close, and help build the enterprise motion from the ground up.

One of the first four Enterprise AEs at a top-tier-VC-backed insurance AI startup. $250K+ ARR deals, OTE $300K–$400K, remote US.

About the company

Early-stage AI company for the insurance industry, backed by top-tier VCs, automating the most tedious paperwork across a $1T+ industry.

Location and employment

Remote · Remote – US (near a major city; travel every 2 weeks) · Full-time

Compensation and work policy

Base salary: $150K–$200K

OTE: $300K–$400K (50/50 split)

Equity: Competitive

Work policy: Remote (US), preferably near a major city; travel every 2 weeks and as needed for customers

Work authorization: US citizens / green card holders only (no visa sponsorship)

• Base $150K–$200K
• OTE $300K–$400K (50/50)
• Competitive equity

Key responsibilities

• Own the end-to-end enterprise cycle: executive discovery, tailored demos, legal and procurement negotiation
• Build relationships across C-suite, operations, finance and IT in large accounts
• Close large, multi-stakeholder deals and hit or exceed revenue targets
• Develop account plans for strategic targets with Product, Engineering and Leadership
• Help define ICPs, sales stages and commercial frameworks
• Surface customer insights that shape the product roadmap

Must-haves

• Proven quota outperformance at a fast-scaling B2B SaaS startup with a strong sales program
• Strong tenure: average 2.5+ years per company

Requirements and qualifications

• 7+ years as an Enterprise AE at fast-scaling B2B SaaS startups
• Closed complex, multi-stakeholder $250K+ ARR deals with long cycles
• Rapid progression at the same company (e.g. SDR to Commercial to Mid-Market to Enterprise)
• Not mainly healthcare-vertical experience; not too senior (e.g. Sales Director)
• Nice to have: selling into commercial insurance or brokerage firms

• 7+ years of enterprise SaaS closing at fast-scaling startups
• History of high ACVs ($250K+) and long sales cycles
• Long tenures with steady promotions
• Comfortable with early-stage ambiguity and frequent travel

Why join

• Be one of the first four Enterprise AEs and shape the GTM playbook
• Sell a product that saves people hours of work every day
• Own complex $250K+ ARR deals with C-suite buyers
• Backed by top-tier VCs

• Be one of the first four Enterprise AEs and shape the GTM playbook
• Sell a product that saves people hours of work every day
• Own complex $250K+ ARR deals with C-suite buyers
• Backed by top-tier VCs

Interview process

• Hiring manager screen
• Hiring manager interview: enterprise deal methodology
• Sales presentation / role play
• Final round: culture and GTM strategy