Enterprise Account Executive, Upper Mid-Market

About the role

Checkr is hiring an Enterprise Account Executive to drive new customer acquisition within companies of 5,000+ employees. This is a full-cycle sales position where you will manage complex deals from initial outreach through post-sale activation. The company provides AI-powered verification services used by over 140,000 organizations including Uber, Pennymac, Airbnb, Doordash, and Anthropic. Checkr appears on the Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

Key facts

What you'll do

• Manage new business sales across 200 to 300 assigned accounts, generating a significant portion of pipeline through your own outbound efforts alongside your BDR partner
• Lead full-cycle Enterprise deals by coordinating across buying committees and internal teams including Product, Sales Engineering, Customer Success, Support, and Executives
• Help prospects calculate their own business challenges by creating quick ROI models during conversations and anchoring deals on financial outcomes rather than product features
• Negotiate and close annual contracts valued between $50K and $1M
• Develop post-sale activation plans before closing, documenting ramp milestones and consumption targets for the Customer Success team
• Apply AI tools in daily operations for account research, pipeline management, and prospecting
• Build internal champions and advocate for resources or approvals when needed
• Travel to meet prospects and customers at events, dinners, or their offices

Requirements

• Track record of closing new Enterprise accounts with complex organizational structures, with multi-year quota attainment you can discuss in detail
• Demonstrated self-sourced outbound motion rather than relying solely on inbound or BDR-generated pipeline
• Experience engaging both EVPs/CXOs and end-users within the same sales cycle using executive-level communication
• Ability to quantify business value and construct ROI cases with prospects
• Background in owning post-sale handoff and ramp planning, ideally within consumptive or volume-based pricing models
• Resourceful approach to finding answers independently without waiting for SE, CS, or BDR availability
• Hands-on operational use of AI tools to increase personal output
• Strong written and verbal communication with the ability to simplify complex subjects
• B2B sales experience, preferably selling to HR buyers
• Action-oriented mindset with urgency, resilience through ambiguity, and ownership of outcomes

Skills & tools

• AI tools for account research, pipeline management, and prospecting
• ROI modeling and financial value quantification
• Multi-threaded Enterprise sales execution
• Executive communication and stakeholder management

Practical notes

• Compensation varies by geographic location
• 100% coverage for medical, dental, and vision
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Learning and development allowance provided
• Monthly wellness stipend included
• Flexible PTO policy
• Competitive equity compensation with advancement opportunities
• Travel required for prospect and customer meetings
• Checkr is committed to fair chance hiring in accordance with local, state, and federal laws including San Francisco's Fair Chance Ordinance