Senior Insurance Trust Account Executive

Checkr, Inc.; Portland (OR); On-site; USD 299,000 - 351,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

Learning & development allowance

Equity compensation

Flexible PTO

Job summary

Checkr Trust is seeking a Senior Account Executive who brings deep insurance industry fluency and a track record of closing six- and seven-figure deals. You will own the insurance vertical, educate the market on a forming category, and drive revenue with autonomy and strategic execution.

This role offers high ownership in a startup-like inside Checkr with enterprise opportunities. You will partner across product, legal, and leadership to shape how we win in insurance, navigate complex buying

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience.
• Deep roots in the insurance industry and knowledge of buying dynamics.
• Experience selling six- or seven-figure deals in complex multi-stakeholder environments.

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, and platforms, then build repeatable motion.
• Leverage existing insurance relationships to accelerate pipeline and shorten deal cycles.
• Own the entire deal lifecycle—from cold outreach to enterprise close.

Skills

Full-cycle sales

Insurance industry

Large deals

AI tactics

Startup mindset

Pipeline building

Targets exceeded

Own the process

Job description

Checkr Trust is seeking a Senior Account Executive who brings deep insurance industry fluency and a track record of closing six- and seven-figure deals. You will own the insurance vertical, educate the market on a forming category, and drive revenue with autonomy and strategic execution.

This role offers high ownership in a startup-like inside Checkr with enterprise opportunities. You will partner across product, legal, and leadership to shape how we win in insurance, navigate complex buying