Senior Account Executive (Insurance)

Join Checkr Trust as a Senior Account Executive in the insurance industry. This high-ownership role requires deep domain fluency and a trusted network. You will own the entire deal lifecycle, educate the market, and hit ambitious revenue targets. Enjoy benefits such as parental leave, stock options, work from home opportunities, comprehensive health plans, competitive compensation, and more.

• Own the insurance vertical by defining ideal customer profiles and building repeatable sales motions.
• Leverage existing insurance relationships to accelerate pipeline and shorten deal cycles, and own the entire deal lifecycle.
• Educate the market on Checkr Trust's value, navigate complex insurance buying processes, and hit ambitious revenue targets.

• Understands insurance workflows well enough to connect Checkr Trust's solutions to real underwriting and risk management problems
• Has worked in a startup or operated like you were in one
• Carries an A-player mindset: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes
• Has 5–7+ years of full-cycle, quota-carrying sales experience — hunting required
• Has deep roots in the insurance industry
• Has outperformed targets in situations that weren't perfectly set up for you
• Has built pipeline when there was no brand awareness in a market
• Has tangible examples of projects created using advanced AI tactics
• Has sold six- or seven-figure deals in complex, multi-stakeholder environments
• You care about building something meaningful, not just closing this quarter's deal
• You have grit. Your energy and work ethic raises the bar of others
• You prefer autonomy and ownership to rigid structure
• You hold yourself to a higher internal standard than anyone else will
• You are comfortable hearing "no" repeatedly without losing momentum
• You don't wait for perfect messaging — you test, iterate, refine
• You understand that building something valuable in a complex, regulated industry like insurance is both rewarding and uncomfortable
• People describe you as relentless, disciplined, competitive — but collaborative