Senior Insurance Enterprise Account Executive

Checkr, Inc.; United States; Hybrid; USD 299,000 - 351,000; Full time

Benefits offered by this job

Learning and development allowance

Competitive cash and equity

Medical, dental, and vision coverage

Relocation stipend

Job summary

Checkr Trust, part of Checkr, is building a new insurance-focused business and seeks a Senior Account Executive who understands insurance and can win in complex, multi-stakeholder environments. You will walk into rooms with carriers, MGAs, or program administrators and gain credibility through domain fluency and networks.

You’ll own the full deal lifecycle—from cold outreach to close—leveraging existing relationships, educating the market, and partnering across product, legal, and leadership to

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience in insurance
• Deep roots in the insurance industry with carrier/MGA/program administrator exposure
• Experience selling six- or seven-figure deals in complex, multi-stakeholder environments
• Ability to translate Checkr Trust value into underwriting, loss prevention, and claims risk language
• Proven track record building pipeline where there was little brand awareness

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program admins, and insurtech platforms, then build repeatable motion
• Leverage existing insurance relationships to accelerate pipeline
• Own the entire deal lifecycle—from cold outreach to multi-threaded close
• Educate the market on a forming category and translate value into underwriting and risk language
• Navigate complex insurance buying processes with underwriting, compliance, legal, and execs
• Experiment with AI to find efficiencies
• Partner cross-functionally with product, legal, operations, and leadership
• Hit ambitious revenue targets

Skills

Insurance industry

Enterprise sales

AI tactics

Startup experience

Relationship building

Job description

Checkr Trust, part of Checkr, is building a new insurance-focused business and seeks a Senior Account Executive who understands insurance and can win in complex, multi-stakeholder environments. You will walk into rooms with carriers, MGAs, or program administrators and gain credibility through domain fluency and networks.

You’ll own the full deal lifecycle—from cold outreach to close—leveraging existing relationships, educating the market, and partnering across product, legal, and leadership to