Enterprise Account Executive (Upper Mid-Market)

Join Checkr as an Enterprise Account Executive, where you'll drive new logo growth within the Enterprise segment. This full-cycle sales role involves building pipeline, running complex sales cycles, and quantifying prospect pain in financial terms. You'll own new business sales across an assigned book of 200-300 accounts, negotiate and close annual contracts ranging from $50K to $1M, and plan for post-sale activation. The ideal candidate is AI-native, resourceful, and has a proven track record of closing new Enterprise accounts.

• Acquisition of new business sales across an assigned book of accounts, with a focus on self-sourcing pipeline.
• Management of full-cycle Enterprise deals, including negotiation and closing of annual contracts ranging from $50K to $1M.
• Collaboration with internal resources and post-sale activation planning to ensure successful implementation and customer satisfaction.
• Operational, hands-on use of AI tools to scale your own output
• Demonstrated ability to quantify business value and build ROI cases with prospects
• Proven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to specifically
• 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
• 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
• Excellent written and verbal communication skills, with the ability to simplify complex topics
• Experience selling to EVPs/CXOs and end-users within the same cycle, and communicating in an executive register
• A real, self-sourced outbound motion — not entirely dependent on inbound or BDR-sourced pipeline
• Experience selling B2B solutions, preferably to HR buyers