Senior InsurTech Account Executive — Remote

Kenyan Edu; San Francisco, Denver, Nashville (CA, CO, TN); Hybrid; USD 299,000 - 351,000; Full time

Benefits offered by this job

Learning and development allowance

Medical, dental, and vision coverage

Equity and compensation growth

Fertility/adoption/parental planning—$

Flexible PTO policy

Monthly wellness stipend

Job summary

Checkr is seeking a Senior Account Executive for Checkr Trust to own the insurance vertical and drive end-to-end deals from cold outreach to close. You will translate Checkr Trust's value into underwriting, loss prevention, and risk management language while building trusted relationships with carriers, MGAs, and program administrators.

The role demands 5–7+ years of full-cycle sales in insurance, a track record of six- or seven-figure deals, startup seasoning, and a bias for using AI to sharpen

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience
• 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 underwriting and risk management problems
• 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 challenging setups
• Has tangible examples of projects created using AI tactics

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms; build repeatable motion
• Leverage existing insurance relationships to accelerate pipeline
• Own the entire deal lifecycle—from cold outreach to close
• Educate the market on a forming category, translating Checkr Trust's value to underwriting and risk management
• Navigate complex buying processes with underwriting, compliance, legal, and executive stakeholders
• Experiment with AI to find efficiencies across your work
• Partner cross-functionally with product, legal, operations, and leadership to win in insurance
• Hit ambitious revenue targets

Skills

Full-cycle sales

Insurance industry experience

Enterprise deals

Pipeline development

Startup experience

AI tactics

Job description

Checkr is seeking a Senior Account Executive for Checkr Trust to own the insurance vertical and drive end-to-end deals from cold outreach to close. You will translate Checkr Trust's value into underwriting, loss prevention, and risk management language while building trusted relationships with carriers, MGAs, and program administrators.

The role demands 5–7+ years of full-cycle sales in insurance, a track record of six- or seven-figure deals, startup seasoning, and a bias for using AI to sharpen