Enterprise Account Executive, Upper Mid-Market

About the role

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.
Quantify prospects' 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.
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.

Pay

On-target Earnings OR Base Salary range (Chicago, IL): $252,697—$297,290 USD
On-target Earnings OR Base Salary range (Dallas, TX): $252,697—$297,290 USD
On-target Earnings OR Base Salary range (Atlanta, GA): $229,724—$270,264 USD

What We Offer

• 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

At Checkr

A fast-paced and collaborative environment
In-office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.

Equal Employment Opportunities

Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.

Applicant Privacy Policy

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