Senior Account Executive, Insurance
Senior Account Executive building Checkr Trust's insurance vertical from the ground up. Owns full deal lifecycle, territory development, and market education for a new AI-powered risk detection solution targeting carriers, MGAs, and insurtech platforms.
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
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