Enterprise Account Executive, Upper Mid-Market

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.

• →Own 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 BDR
• →Run 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 close
• →Get prospects to quantify their own pain — build simple, back-of-napkin ROI models in real time and anchor the close on financial outcomes, not features
• →Negotiate and close annual contracts ranging $50K–$1M
• →Own post-sale activation planning — document ramp milestones and consumption targets before the deal closes, and set the CS team up to execute against them
• →Use AI tools operationally to run your business — account research, pipeline management, and prospecting, not just experimentation
• →Develop internal champions and sell the deal internally when you need resources or approvals
• →Travel to meet prospects and customers at events, meals, or their facilities

• Proven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to specifically
• A real, self-sourced outbound motion — not entirely dependent on inbound or BDR-sourced pipeline
• Experience selling to EVPs/CXOs and end-users within the same cycle, and communicating in an executive register
• Demonstrated ability to quantify business value and build ROI cases with prospects
• Experience owning post-sale handoff and ramp/activation planning, ideally in a consumptive or volume-based pricing model
• Resourcefulness — you find the answer rather than waiting for SE/CS/BDR bandwidth that isn't guaranteed
• Operational, hands-on use of AI tools to scale your own output
• Excellent written and verbal communication skills, with the ability to simplify complex topics
• Experience selling B2B solutions, preferably to HR buyers
• An 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 outcomes

We 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, see our website.