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About the Role

Checkr Trust is building a new business focused on insurance, aiming to accelerate solutions that detect bad actors before they impact businesses. This role offers a unique opportunity to operate like a founder within an established company, with significant ownership and impact in a developing market.

Responsibilities

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms — then build repeatable motion where none exists yet
• 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 to shape how we win in insurance
• Hit ambitious revenue targets

Requirements

• 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
• Built pipeline when there was no brand awareness in a market
• Worked in a startup or operated like you were in one
• Outperformed targets in situations that weren't perfectly set up for you
• 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 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 self to a higher internal standard than anyone else will
• Relentless, disciplined, competitive — but collaborative
• Understands that building something valuable in a complex, regulated industry like insurance is both rewarding and uncomfortable

Skills

• Sales
• Insurance industry knowledge
• AI tactics

Location

• San Francisco, CA

Work Type

• Onsite (3+ days a week)
• Full-time

Experience Level

• Senior
• 5-7+ years of sales experience

Salary/Compensations

• $258,000—$304,000 USD (On-target Earnings OR Base Salary range)

Benefits

• Learning and development allowance
• Competitive cash and equity compensation
• 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

About the Company

• Checkr is building the data platform to power safe and fair decisions.
• Over 140,000 companies and millions of people rely on Checkr for AI verification.
• Customers include Uber, Pennymac, Airbnb, Doordash, Amazon, and Anthropic.
• Recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

Equal Opportunity

• Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences.
• Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.