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

Benefits

• Parental leave
• Stock optoins
• Work from home opportunities
• Comprehensive Health Plans | We cover 100% of insurance premiums and offer generous parental and family leave
• Competitive Compensation | We offer competitive salaries and meaningful equity
• A Variety of Food and Snacks | Our culinary team serves a rotating menu for lunch each day, along with unlimited snacks and drinks
• Wellness Programs | We invest in the holistic well-being of every team member through education reimbursements, onsite massages, and physical therapy
• Flexible Paid Time Off | We want you to take the time you need to relax and recharge
• Fitness and Public Transport Reimbursement | We’ll cover your commute and help you stay active with our onsite gym or fitness provider of choice

• Experience selling B2B solutions, preferably to HR buyers
• 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
• 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
• Experience selling to EVPs/CXOs and end-users within the same cycle, and communicating in an executive register
• 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
• Proven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to specifically
• Excellent written and verbal communication skills, with the ability to simplify complex topics
• A real, self-sourced outbound motion — not entirely dependent on inbound or BDR-sourced pipeline