Enterprise Account Executive

Checkr • Chicago, IL

6h • $240,943 - $311,808 • Hybrid

About The Position

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.

Requirements

• 7+ years of experience selling B2B solutions, preferably to HR buyers
• 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
• 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

Responsibilities

• 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

• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend
• Lunch five times a week
• Commuter stipend
• Relocation stipend may be available

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed