Senior Account Executive, Insurance

What You'll Do

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms — then build repeatable motion where none exists yet
• Leverage your existing insurance relationships to accelerate pipeline and shorten deal cycles
• Own the entire deal lifecycle — from cold outreach to multi-threaded enterprise close
• Educate the market on a category that is still forming, translating Checkr Trust's value into the language of underwriting, loss prevention, and claims risk
• Navigate complex insurance buying processes involving 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 shape how we win in insurance
• Hit ambitious revenue targets

What We're Looking For

• 5–7+ years of full-cycle, quota-carrying sales experience — hunting required
• 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 real underwriting and risk management problems
• Has 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 situations that weren't perfectly set up for you
• Has tangible examples of projects created using advanced AI tactics
• Carries an A-player mindset: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes
• Grit, energy, and work ethic that raises the bar of others
• Prefers autonomy and ownership to rigid structure
• Doesn't wait for perfect messaging — tests, iterates, refines
• Comfortable hearing "no" repeatedly without losing momentum
• Cares about building something meaningful, not just closing this quarter's deal
• Holds themselves to a higher internal standard than anyone else will

What We Offer

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend
• In-office perks: lunch five times a week, commuter stipend, snacks and beverages
• Relocation stipend may be available for those willing to relocate to a Checkr hub location