Job Details

Enterprise Account Executive

AI × Insurance | High-Value Deals | Build the Enterprise Motion

Hybrid | San Francisco OR NYC | $350K+ OTE (uncapped commission)

The client is hiring an Enterprise Account Executive to help scale a fast-growing AI company operating in one of the most complex and opportunity-rich industries: insurance.

This role is critical to expanding market presence, landing flagship enterprise logos, and shaping how AI is sold into a traditionally conservative vertical. You'll own meaningful deals, influence GTM strategy, and help professionalize the enterprise sales motion as the company scales.

If you're a strong closer who thrives in ambiguity and wants real ownership, not just quota, this is the role.

AI in a High-Stakes Industry

You'll sell AI-native solutions into the insurance ecosystem-complex workflows, risk-sensitive buyers, and real transformation potential.

Real Revenue Ownership

This is a full-cycle role with meaningful ARR responsibility, expansion upside, and a direct line between your execution and company growth.

Build While You Sell

You won't inherit a static playbook. You'll help refine messaging, pricing, and positioning based on what the market is actually telling you.

Flagship Logos, Not Volume Selling

Success here means landing and expanding strategic enterprise accounts-not chasing SMB deal counts.

What You'll Do

Own the Full Sales Cycle

• Manage deals from qualified lead through discovery, demo, proposal, negotiation, and close
• Partner with SDRs and marketing to develop and convert high-quality pipeline

Run Consultative Enterprise Sales

• Quickly learn prospect workflows and pain points
• Position solutions with credibility to insurance buyers and operators

Operate with Rigor

• Maintain a clean, accurate pipeline and forecasts in CRM
• Deliver reliable quarterly forecasts and deal progression

Shape the Go-To-Market Motion

• Actively contribute to messaging, positioning, and pricing evolution
• Provide structured feedback based on live deal learnings

How You'll Be Measured

Land New ARR & Flagship Logos

• Consistently meet or exceed new-logo ARR targets
• Close enterprise customers within the target insurance segment

Build a Healthy Pipeline

• Maintain 3-4× pipeline coverage with a mix of self-sourced and SDR-sourced opportunities
• Demonstrate consistent stage progression without stalled deals

Improve Sales Efficiency

• Shorten average sales cycle
• Improve stage-to-stage conversion rates
• Forecast within ±20% accuracy

Drive Strong Post-Sale Outcomes

• Ensure clean handoffs to CSM/AM with expansion opportunities identified early
• Support strong year-one renewals and account growth

Deliver Market Intelligence

• Produce quarterly "voice of customer" insights
• Surface objections, competitor signals, and product requests
• Influence roadmap and GTM strategy with 2-3 adopted insights per quarter

Who Thrives Here

Seniority & Experience

• 3+ years of full-cycle closing experience as an Enterprise AE at a tech startup
• History of consistent promotions and increased responsibility

Work Experience

• Experience closing $100K+ ACV deals
• Proven ability to manage $1M+ quotas with expansion potential
• Background selling into the insurance vertical or prior insurance experience

Education

• Undergraduate degree

Hard Skills

• Strong proficiency with CRM and sales automation tools (e.g., HubSpot, Apollo)

Soft Skills

• Comfortable with ambiguity and building sales processes
• Strong communicator with high IQ and EQ
• Consultative, credible, and outcome-oriented

Not a Fit If You're...

• Frequently changing roles (we're looking for 2-3+ years of tenure per role)
• Uncomfortable owning complex deals end-to-end
• Looking for a highly structured, fully built enterprise sales org

Why This Role Is Rare

• AI + insurance is early, complex, and wide open
• Real ownership of enterprise deals and GTM evolution
• Opportunity to help define how this category is sold
• Clear path to growth as the enterprise motion scales

If you want to build and close meaningful enterprise deals in an emerging AI category-and have your execution materially shape the business-this is a role worth exploring.

Apply or reach out directly to learn more - ...@motivityresources.com