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About CheckrCheckr 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 in the moments that matter most: getting a new job, a new place to live, a car ride, childcare, even a date. Customers include Uber, Pennymac, Airbnb, Doordash, and Anthropic.We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.About the team/roleCheckr Trust is not a typical sales role. It's a chance to help build an entirely new business inside a category-defining company — and we're going deep on insurance.Checkr Trust accelerates solutions that detect bad actors before they impact businesses. We have early traction in the insurance space, strong product-market pull, and the backing of Checkr — but we are still building the plane while flying it.We are looking for a Senior Account Executive who knows the insurance industry from the inside: the players, the pain points, the buying dynamics, and the relationships. Someone who can walk into a room with a carrier, MGA, or program administrator and immediately earn credibility — not because of a slide deck, but because of deep domain fluency and a trusted network.This role is for someone who wants:A difficult, high-ownership roleAmbiguity over predictabilityAccountability over excusesLong-term impact over short-term comfortThis is not a "manage a book of inbound" job. 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 — except you have the resources of an established company behind you.If you want something safe and structured, this won't be the right fit. If you want to build something enduring in insurance — and are willing to do the hard work required — keep reading.What You'll DoOwn the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms — then build repeatable motion where none exists yetLeverage your existing insurance relationships to accelerate pipeline and shorten deal cyclesOwn the entire deal lifecycle — from cold outreach to multi-threaded enterprise closeEducate the market on a category that is still forming, translating Checkr Trust's value into the language of underwriting, loss prevention, and claims riskNavigate complex insurance buying processes involving underwriting, compliance, legal, and executive stakeholdersExperiment with AI to find efficiencies across your workPartner cross-functionally with product, legal, operations, and leadership to shape how we win in insuranceHit ambitious revenue targetsYour fingerprints will be on how Checkr Trust wins in insurance.What We're Looking ForYou are someone who:Has 5–7+ years of full-cycle, quota-carrying sales experience — hunting requiredHas deep roots in the insurance industryHas sold six- or seven-figure deals in complex, multi-stakeholder environmentsUnderstands insurance workflows well enough to connect Checkr Trust's solutions to real underwriting and risk management problemsHas built pipeline when there was no brand awareness in a marketHas worked in a startup or operated like you were in oneHas outperformed targets in situations that weren't perfectly set up for youHas tangible examples of projects created using advanced AI tacticsCarries an A-player mindset: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomesMore importantly:You have grit. Your energy and work ethic raises the bar of othersYou prefer autonomy and ownership to rigid structureYou don't wait for perfect messaging — you test, iterate, refineYou are comfortable hearing "no" repeatedly without losing momentumYou care about building something meaningful, not just closing this quarter's dealYou hold yourself to a higher internal standard than anyone else willPeople describe you as relentless, disciplined, competitive — but collaborative. You understand that building something valuable in a complex, regulated industry like insurance is both rewarding and uncomfortable.What We OfferA fast-paced and collaborative environmentLearning and development allowanceCompetitive cash and equity compensation, and opportunity for advancement100% medical, dental, and vision coverageUp to $25K reimbursement for fertility, adoption, and parental planning servicesFlexible PTO policyMonthly wellness stipendAt Checkr, we believe an in office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.
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