Senior Insurance Solutions Account Executive

Checkr; San Francisco, Northern (CA, KY); Hybrid; USD 299,000 - 351,000; Full time

Benefits offered by this job

Learning allowance

Equity

Medical coverage

Fertility & parental support

Flexible PTO

Job summary

Checkr Trust is seeking a Senior Account Executive in San Francisco to own the insurance vertical, build a repeatable sales motion, and leverage existing relationships to drive multi-million-dollar opportunities. You will close end-to-end deals, educate the market on a developing category, and collaborate with product, legal, and leadership.

You’ll operate like a founder within Checkr Trust, leveraging AI to improve efficiency and win in a complex, regulated industry while delivering meaningful

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience in insurance.
• Deep roots in the insurance industry with carrier/MGA knowledge.
• Track record of closing six- or seven-figure deals in multi-stakeholder settings.
• Ability to map Checkr Trust's solutions to underwriting and risk management needs.
• Experience building pipeline in a low-brand market and operating like a startup.

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program admins, and insurtech platforms.
• Build repeatable motion where none exists yet to accelerate growth.
• Leverage existing insurance relationships to speed up pipeline and shorten cycles.
• Own the full deal lifecycle from cold outreach to multi-threaded close.
• Educate the market on a forming category, translating value to underwriting and claims risk.
• Collaborate cross-functionally with product, legal, operations, and leadership.

Skills

Full-cycle sales

Quota carrying

Insurance industry experience

Six-figure deals

AI-driven selling

Job description

Checkr Trust is seeking a Senior Account Executive in San Francisco to own the insurance vertical, build a repeatable sales motion, and leverage existing relationships to drive multi-million-dollar opportunities. You will close end-to-end deals, educate the market on a developing category, and collaborate with product, legal, and leadership.

You’ll operate like a founder within Checkr Trust, leveraging AI to improve efficiency and win in a complex, regulated industry while delivering meaningful