Remote InsurTech Enterprise Account Executive

Checkr; United States; Remote; USD 230,000 - 351,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Learning and development allowance

Competitive cash and equity

Relocation stipend may be available

Flexible PTO policy

Monthly wellness stipend

Job summary

Checkr Trust is seeking a Senior Account Executive to own the insurance vertical, build credibility with carriers and MGAs, and educate the market about a category still forming. You’ll act like a founder inside a startup while supported by Checkr’s resources.

You will leverage deep insurance relationships to accelerate pipeline, close six- to seven-figure deals in complex multi-stakeholder environments, and partner with product, legal, and leadership to shape how we win in insurance.

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience in insurance.
• Deep roots in the insurance industry with carrier/MGA/program admin exposure.
• Experience selling six- or seven-figure deals in multi-stakeholder environments.
• Ability to translate insurance workflows into underwriting and risk management value.
• Built pipeline in a market with little prior brand awareness.
• Experience working in or like a startup; high ownership.

Responsibilities

• Own the insurance vertical by defining ICPs and building repeatable motion.
• Leverage existing insurance relationships to accelerate pipeline.
• Manage the full deal lifecycle from cold outreach to close.
• Educate the market on a forming category with underwriting terms.
• Navigate complex buying processes with multiple stakeholders.
• Experiment with AI to find efficiencies.
• Collaborate with product, legal, operations, and leadership.
• Hit ambitious revenue targets.

Skills

Insurance sales

Full-cycle sales

Enterprise deals

Industry knowledge

AI tactics

Startup experience

Relationship building

Negotiation

Job description

Checkr Trust is seeking a Senior Account Executive to own the insurance vertical, build credibility with carriers and MGAs, and educate the market about a category still forming. You’ll act like a founder inside a startup while supported by Checkr’s resources.

You will leverage deep insurance relationships to accelerate pipeline, close six- to seven-figure deals in complex multi-stakeholder environments, and partner with product, legal, and leadership to shape how we win in insurance.