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StradaStrada

Enterprise Account Executive

Enterprise Account Executive selling AI agents for insurance operations (quoting, servicing, claims) to carriers, brokers, and TPAs. Owns full sales cycle from discovery to close with operations and transformation leaders; requires 5+ years B2B enterprise sales experience closing 6-7 figure deals.

About the job

Responsibilities

  • Driving new business with Operations, Claims, and Transformation leaders at large insurance carriers, brokers, wholesalers, and TPAs.
  • Running discovery and consultative demos that uncover inefficiencies in claims handling, customer service, and quote intake.
  • Mapping complex org structures and building multi-threaded relationships with both technical and business leaders.
  • Collaborating with product and engineering to communicate customer feedback and influence roadmap priorities.
  • Managing a clean, high-velocity pipeline in HubSpot with precision forecasting.
  • Closing deals that help insurance leaders scale service, reduce costs, and delight policyholders.
  • Acting as a trusted advisor, not a vendor, guiding customers through the path from manual service to AI automation.

Requirements

  • 5+ years of B2B enterprise sales experience, with a proven track record of exceeding quota.
  • Experience selling technical products to operations leaders, preferably in the insurance industry.
  • A strong understanding of complex sales processes with 6-figure to 7-figure ACVs.
  • A consultative approach and meticulous attention to detail, simplifying complexity, and earning trust.
  • A growth mindset, hungry to learn, iterate, and drive to perfect your GTM strategy.
  • Grit, resilience, and the ability to navigate long cycles and multiple stakeholders.

Nice-to-Haves

  • Experience selling enterprise software to the insurance industry.
  • Founding sales team or early-stage startup experience.

Compensation and Benefits

  • Top-of-market salary and uncapped OTE.
  • Meaningful equity stake with significant upside.
  • Comprehensive medical, dental, and vision insurance.
  • Flexible time off and paid holidays.

Skills

Enterprise Sales, B2B Sales, Sales Pipeline Management, HubSpot, Consultative Selling, Go-to-Market Strategy

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