Senior Account Executive, InsurTech

Senior Account Executive, InsurTech

Checkr is seeking a Senior Account Executive to help build and scale the insurance vertical within Checkr Trust. This role involves defining ICPs, building pipeline, owning the deal lifecycle, and educating the market on the value of Checkr Trust's solutions in the insurance industry.

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms.
• Leverage existing insurance relationships to accelerate pipeline and shorten deal cycles.
• Own the entire deal lifecycle — from cold outreach to multi-threaded enterprise close.
• Educate the market on a category that is still forming, translating Checkr Trust's value into the language of underwriting, loss prevention, and claims risk.
• Navigate complex insurance buying processes involving underwriting, compliance, legal, and executive stakeholders.
• Partner cross-functionally with product, legal, operations, and leadership to shape how we win in insurance.
• Hit ambitious revenue targets.

Requirements

• 5–7+ years of full-cycle, quota-carrying sales experience — hunting required.
• Deep roots in the insurance industry.
• Sold six- or seven-figure deals in complex, multi-stakeholder environments.
• Understands insurance workflows well enough to connect Checkr Trust's solutions to real underwriting and risk management problems.
• Has built pipeline when there was no brand awareness in a market.
• Has worked in a startup or operated like you were in one.
• Has outperformed targets in situations that weren't perfectly set up for you.
• Has tangible examples of projects created using advanced AI tactics.
• A-player mindset: raises the bar, moves with urgency, stays resilient through ambiguity, and takes ownership to deliver meaningful outcomes.
• Grit, autonomy, and a preference for ownership over structure.
• Comfort with rejection and a focus on long-term impact over short-term comfort.
• Holds oneself to a higher internal standard than anyone else will.
• Described as relentless, disciplined, competitive, and collaborative.

Salary On-target Earnings OR Base Salary range (Remote): $229,724 — $351,343 USD

How to Apply Apply via Checkr's careers page.