Senior Insurance Growth Executive

Checkr; Northern (KY); Hybrid; USD 230,000 - 351,000; Full time

Benefits offered by this job

Medical coverage

Dental coverage

Vision coverage

Equity compensation

Fertility/adoption reimbursement

Flexible PTO

Learning allowance

Wellness stipend

In-office perks

Job summary

Checkr Trust is seeking a Senior Account Executive who brings deep insurance industry knowledge to build and own a new insurance vertical. You will define ICPs across carriers and MGAs, leverage relationships to accelerate pipeline, and guide complex multistakeholder deals from first outreach to close.

This is a founder-like role within a startup inside Checkr, demanding autonomy, resilience, and the ability to educate the market on a forming category.

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience, hunting required.
• Deep roots in the insurance industry.
• Sold six- to seven-figure deals in complex, multi-stakeholder environments.
• Understands insurance workflows to connect Checkr Trust solutions to underwriting and risk management.
• Built pipeline when there was no brand awareness in a market.
• Worked in a startup or operated like you were in one with urgency and ownership.
• Has tangible examples of projects using advanced AI tactics.

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms, then build repeatable motion where none exists yet.
• 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 still forming, translating Checkr Trust's value into underwriting and risk language.
• Navigate complex insurance buying processes involving underwriting, compliance, legal, and executives.
• Experiment with AI to find efficiencies across your work.
• Partner cross-functionally with product, legal, operations, and leadership to shape how we win in insurance.

Skills

Full-cycle sales

Insurance know-how

Enterprise deals

AI tactics

Networking

Startup mindset

Job description

Checkr Trust is seeking a Senior Account Executive who brings deep insurance industry knowledge to build and own a new insurance vertical. You will define ICPs across carriers and MGAs, leverage relationships to accelerate pipeline, and guide complex multistakeholder deals from first outreach to close.

This is a founder-like role within a startup inside Checkr, demanding autonomy, resilience, and the ability to educate the market on a forming category.