Senior Account Executive, Insurance Trust — Territory Builder

Checkr, Inc.; Denver (CO); On-site; USD 230,000 - 360,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

Wellness stipend

Learning & development allowance

Fertility/adoption support

Job summary

Checkr Trust is building a new, high-ownership insurance vertical inside Checkr. You will own ICPs, leverage relationships, and drive end-to-end deals from cold outreach to close in a founder-like role backed by an established company.

You will operate in a challenging, fast-paced environment, with aggressive revenue targets and the opportunity to shape how we win in insurance through AI-enabled selling and cross-functional collaboration.

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience in insurance
• Deep roots in the insurance industry with strong relationship-building
• Experience closing six- or seven-figure deals in complex, multi-stakeholder environments

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program admins, and insurtech platforms
• Build repeatable motion where none exists yet
• Leverage existing insurance relationships to accelerate pipeline
• Own the entire deal lifecycle—from cold outreach to multi-threaded enterprise close
• Educate the market on a forming category in underwriting terms
• Navigate underwriting, compliance, legal, and executive stakeholders
• Experiment with AI to find efficiencies in work
• Partner cross-functionally with product, legal, operations, and leadership
• Hit ambitious revenue targets

Skills

Full-cycle sales

Insurance industry

Six- to seven-figure deals

Underwriting/risk knowledge

Startup mindset

Quota achievement

AI-enabled selling

Autonomy and ownership

Job description

Checkr Trust is building a new, high-ownership insurance vertical inside Checkr. You will own ICPs, leverage relationships, and drive end-to-end deals from cold outreach to close in a founder-like role backed by an established company.

You will operate in a challenging, fast-paced environment, with aggressive revenue targets and the opportunity to shape how we win in insurance through AI-enabled selling and cross-functional collaboration.