Senior Account Executive

Checkr is building the data platform to power safe and fair decisions. Over 140,000 companies rely on Checkr for AI verification in moments like getting a new job, a place to live, a car ride, childcare, or a date. Customers include Uber, Pennymac, Airbnb, Doordash, and Anthropic. Checkr is on the Forbes Cloud 100 2025 List and a Y Combinator 2024 Breakthrough Company.

Checkr Trust is a new business inside Checkr, focused on insurance. We are looking for a Senior Account Executive who knows the insurance industry from the inside: players, pain points, buying dynamics, and relationships. This is a territory-building, market-educating, first-call-to-close ownership role within the insurance vertical. You will operate like a founder inside a startup with the resources of an established company.

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms, and build repeatable motion.
• Leverage 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.
• Hit ambitious revenue targets.

• 5–7+ years of full-cycle, quota-carrying sales experience — hunting required.
• Deep roots in the insurance industry.
• Has sold six- or seven-figure deals in complex, multi-stakeholder environments.
• Understands insurance workflows to connect solutions to 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 one.
• Has outperformed targets in situations that weren't perfectly set up.
• Has tangible examples of projects created using advanced AI tactics.
• Carries an A-player mindset: raises the bar, moves with urgency, resilient through ambiguity, takes ownership.

On-target Earnings OR Base Salary range (San Francisco, CA): $258,000—$304,000 USD.

• Learning and development allowance
• Competitive cash and equity compensation
• 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
• A relocation stipend may be available for those willing to relocate to a Checkr hub location.

Hybrid - expected to work from the office 3+ days a week. Hub locations: Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. This role is based in San Francisco, CA.

Apply via the Greenhouse posting.