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Full-time · On-site

Enterprise Account Executive

This is a high-stakes sales role for a profitable, AI-native startup that has already demonstrated massive market fit within the insurance industry. Candidates will manage massive deal sizes and enjoy significant autonomy in shaping the sales playbook. It is a perfect blend of early-stage equity upside and the stability of a revenue-positive business.

Kyber · New York, New York, United States · Posted 19 April 2026

The role

Overview

This is a high-stakes sales role for a profitable, AI-native startup that has already demonstrated massive market fit within the insurance industry. Candidates will manage massive deal sizes and enjoy significant autonomy in shaping the sales playbook. It is a perfect blend of early-stage equity upside and the stability of a revenue-positive business.

What they need

Requirements & Skills

Key Responsibilities

  • Own the end-to-end sales cycle from lead generation to closing
  • Develop and execute creative outbound strategies including 'guerilla' marketing and in-person visits
  • Build and maintain relationships with C-level decision makers in the insurance space
  • Collaborate with the GTM team to refine messaging and forecast pipeline health
  • Represent the brand at major industry events and conferences

Essential

  • Minimum of 3 years of professional experience
  • Proven track record in managing full-cycle enterprise sales processes
  • Ability to navigate complex, multi-threaded stakeholder environments
  • Experience with outbound prospecting including cold calling and LinkedIn outreach
  • US Citizen or valid US work visa holder
  • Willingness to travel for in-person meetings and industry conferences

Preferred

  • Experience in the insurance or regulatory technology sector
  • Familiarity with AI-native sales tools and SDR automation
  • Background in high-growth, venture-backed startup environments
  • Experience closing six and seven-figure multi-year contracts

Key Skills

Enterprise Sales StrategyOutbound ProspectingHubSpot CRMBusiness Case DevelopmentContract NegotiationStakeholder ManagementPublic Speaking and PresentationsAI-SDR Tooling (e.g., 11x)Strategic Account Planning

Networking

People to Know

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Perks

Benefits & perks

  • Competitive base salary and commission structure
  • Significant equity ownership (0.05% - 0.25%)
  • Direct access to founders and YC network
  • Opportunity to work in a profitable, high-growth startup
  • Strategic involvement in GTM and product feedback loops

Next step

Apply now

Found via www.ycombinator.com