Enterprise Account Executive, Upper Mid-Market
Full-cycle Enterprise Account Executive owning new logo sales (>5K employee companies) at Checkr. Responsibilities include self-sourced outbound pipeline, complex deal orchestration, real-time ROI modeling, contract negotiation up to $1M, and post-sale activation planning. Requires proven enterprise quota attainment, executive selling skills, and hands-on AI tool usage.
About the job
What you'll do
- 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
What you bring
- 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
What We Offer
- A fast-paced and collaborative environment
- 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
Skills
Sales, Outbound Sales, Roi Modeling, Enterprise Sales, CRM, AI Tools, B2B Sales, Negotiation, Account Management, Pipeline Management, Hr Tech
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