Enterprise Account Executive - AI-Powered Growth

Diiirect Inc.; Dallas, Northern (GA, KY); Hybrid; USD 265,000 - 312,000; Full time

Benefits offered by this job

Learning and development allowance

Competitive cash and equity

100% medical, dental, and vision

Job summary

Checkr is seeking an Enterprise Account Executive to own new logo growth within the Enterprise segment, managing 200–300 accounts with a self-sourced outbound motion. You will lead full-cycle deals, coordinate with cross-functional teams, and quantify ROI to drive the close.

You will negotiate large contracts and plan post-sale activation, using AI tools to streamline research and pipeline management. A strong executive presence and industry experience are essential for success.

Qualifications

• 7+ years of experience selling B2B solutions.
• Proven track record closing new Enterprise accounts with multi-year quotas.
• Self-sourced outbound motion not dependent on inbound pipeline.
• Experience selling to EVPs/CXOs and end-users in the same cycle.
• Ability to quantify business value and build ROI cases.
• Experience owning post-sale ramp/activation planning.
• Resourcefulness in finding answers without relying on others.
• Hands-on use of AI tools to scale output.
• Excellent written and verbal communication; ability to simplify complex topics.
• A high-action, resilient mindset with ownership and urgency.

Responsibilities

• Own new business sales across an assigned book (200–300 accounts) and build pipeline with your outbound motion.
• Run full-cycle Enterprise deals, coordinating with Product, SE, CS, Support, and Executives to close.
• Quantify prospect pain and anchor the close on financial outcomes rather than features.
• Negotiate and close annual contracts ranging $50K–$1M.
• Own post-sale activation planning and document ramp milestones.
• Use AI tools for account research, pipeline management, and prospecting.
• Develop internal champions and secure resources or approvals as needed.
• Travel to meet prospects and customers at events, meals, or facilities.

Skills

B2B sales

Enterprise deals

Outbound sales

Executive communication

ROI modeling

Post-sale handoff

AI tools

Job description

Checkr is seeking an Enterprise Account Executive to own new logo growth within the Enterprise segment, managing 200–300 accounts with a self-sourced outbound motion. You will lead full-cycle deals, coordinate with cross-functional teams, and quantify ROI to drive the close.

You will negotiate large contracts and plan post-sale activation, using AI tools to streamline research and pipeline management. A strong executive presence and industry experience are essential for success.