Enterprise Account Executive, Upper Mid-Market (Chicago)

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, Amazon, 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.As an Enterprise Account Executive, you'll own new logo growth within Checkr's Enterprise segment (>5K employees). This is a full-cycle, high-complexity sales role — you'll build pipeline, run sophisticated sales cycles, quantify prospect pain in financial terms, and stay accountable for the deal through post-sale activation. We're looking for someone who is AI-native, resourceful, and treats ramp and adoption as part of the sale, not someone else's problem.What you'll doOwn new business sales across an assigned book (200–300 accounts), with a meaningful share of pipeline self-sourced through your own outbound motion, in partnership with your BDRRun full-cycle Enterprise deals — multi-thread across the buying committee, quarterback internal resources (Product, SE, CS, Support, Executives), and orchestrate the deal from first outbound to closeGet prospects to quantify their own pain — build simple, back-of-napkin ROI models in real time and anchor the close on financial outcomes, not featuresNegotiate and close annual contracts ranging $50K–$1MOwn post-sale activation planning — document ramp milestones and consumption targets before the deal closes, and set the CS team up to execute against themUse AI tools operationally to run your business — account research, pipeline management, and prospecting, not just experimentationDevelop internal champions and sell the deal internally when you need resources or approvalsTravel to meet prospects and customers at events, meals, or their facilitiesWhat you bringProven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to specificallyA real, self-sourced outbound motion — not entirely dependent on inbound or BDR-sourced pipelineExperience selling to EVPs/CXOs and end-users within the same cycle, and communicating in an executive registerDemonstrated ability to quantify business value and build ROI cases with prospectsExperience owning post-sale handoff and ramp/activation planning, ideally in a consumptive or volume-based pricing modelResourcefulness — you find the answer rather than waiting for SE/CS/BDR bandwidth that isn't guaranteedOperational, hands-on use of AI tools to scale your own outputExcellent written and verbal communication skills, with the ability to simplify complex topicsExperience selling B2B solutions, preferably to HR buyersAn A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomesPay Transparency DisclosureWe use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, seeour website.On-target Earnings OR Base Salary range (Chicago, IL)$252,697—$297,290 USDOn-target Earnings OR Base Salary range (Dallas, TX)$252,697—$297,290 USDOn-target Earnings OR Base Salary range (Atlanta, GA)$229,724—$270,264 USDWhat 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.Equal Employment Opportunities at CheckrCheckr 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.Applicant Privacy PolicyIf you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.*Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., View email address on apply.placed-app.com or View email address on apply.placed-app.com).