Enterprise Account Executive, Upper Mid-Market

About the role

Checkr is seeking an Enterprise Account Executive to spearhead customer acquisition efforts targeting organizations with over 5,000 employees. This position encompasses the entire sales cycle, allowing you to oversee intricate deals from the initial outreach phase all the way through to post-sale implementation. Checkr offers AI-driven verification services that are utilized by more than 140,000 companies, including notable names such as Uber, Pennymac, Airbnb, Doordash, and Anthropic. The company has been recognized on the Forbes Cloud 100 list for 2025 and has been identified as a Breakthrough Company by Y Combinator in 2024.

Key facts

What you'll do

• Oversee new business sales across a portfolio of 200 to 300 assigned accounts, significantly contributing to your pipeline through proactive outbound efforts in collaboration with your Business Development Representative (BDR) partner.
• Lead comprehensive Enterprise sales processes by coordinating with various stakeholders, including Product, Sales Engineering, Customer Success, Support, and Executive teams.
• Assist potential clients in assessing their business challenges by developing quick ROI models during discussions, focusing on financial outcomes rather than just product features.
• Negotiate and finalize annual contracts ranging from $50,000 to $1 million.
• Create post-sale activation strategies prior to closing deals, outlining ramp milestones and consumption targets for the Customer Success team.
• Utilize AI tools in your daily activities for account research, pipeline management, and prospecting efforts.
• Cultivate internal champions within client organizations and advocate for necessary resources or approvals as required.
• Travel to meet with prospects and customers at events, dinners, or their offices to foster relationships and facilitate discussions.

Requirements

• Proven history of successfully closing new Enterprise accounts within complex organizational frameworks, with detailed multi-year quota achievements to discuss.
• Demonstrated ability to self-source leads and drive outbound sales efforts rather than relying solely on inbound inquiries or leads generated by BDRs.
• Experience engaging with both executive-level decision-makers (EVPs/CXOs) and end-users throughout the same sales cycle, employing effective communication strategies.
• Capability to quantify business value and construct compelling ROI cases during discussions with prospects.
• Experience managing post-sale transitions and ramp planning, ideally within pricing models that are consumptive or volume-based.
• Resourcefulness in independently seeking answers and solutions without waiting for assistance from Sales Engineers, Customer Success, or BDRs.
• Proficient in the operational use of AI tools to enhance personal productivity and efficiency.
• Excellent written and verbal communication skills, with the ability to simplify complex topics for diverse audiences.
• B2B sales experience is preferred, particularly in selling to HR professionals.
• A proactive, action-oriented mindset characterized by urgency, resilience in uncertain situations, and a strong sense of ownership over outcomes.

Nice to have

• Familiarity with the HR technology landscape and trends.
• Experience in a fast-paced startup environment.
• Background in technology sales, particularly in software or SaaS solutions.
• Knowledge of compliance and background check processes.
• Previous experience with account-based marketing strategies.

Skills & tools

• Proficient in AI tools for account research, pipeline management, and prospecting.
• Expertise in ROI modeling and financial value assessment.
• Strong capabilities in executing multi-threaded Enterprise sales strategies.
• Excellent executive communication skills and stakeholder management abilities.

Practical notes

• Compensation varies based on geographic location and market standards.
• Comprehensive coverage for medical, dental, and vision insurance.
• Up to $25,000 reimbursement available for fertility, adoption, and parental planning services.
• A dedicated budget for learning and development opportunities is provided.
• Monthly wellness stipend included to promote employee well-being.
• Flexible paid time off (PTO) policy to support work-life balance.
• Competitive equity compensation with opportunities for career advancement.
• Travel is required for meetings with prospects and customers.
• Checkr is committed to fair chance hiring practices in compliance with local, state, and federal regulations, including San Francisco's Fair Chance Ordinance.