Enterprise Account Executive, Upper Mid-Market

Remote, United Statesfull time

Remote

$50k

H1B: yes

Checkr Enterprise Account Executive at Checkr owns new logo growth within the Enterprise segment, managing full-cycle sales and building pipeline through outbound motion. The role requires quantifying prospect pain in financial terms and managing post-sale activation.

Responsibilities

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
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

Qualification

Multi-year quota attainmentSelf-sourced outbound motionOperational

Required

Proven track record closing new Enterprise accounts with complex organizational structures
Multi-year quota attainment
Self-sourced outbound motion
Experience selling to EVPs/CXOs and end-users within the same cycle
Ability to quantify business value and build ROI cases
Experience owning post-sale handoff and ramp/activation planning
Operational, hands-on use of AI tools
Excellent written and verbal communication skills

Benefits

Dental
Vision
PTO
Equity/RSU
Wellness

Company

Checkr

View company page

Source: greenhouse

Active within the past hour

Remote-friendly

More roles at Checkr

Head of Pricing Strategy

San Francisco

Senior Performance Marketing Manager

Remote, United States

Staff Data Engineer

San Francisco

Staff Product Manager, Hiring Fraud Solutions

Denver

Boost Your Interview Chances

Improve Resume Match Score

Free

Your Score

9.0

Strong Applicant

Must-Have Skills for This Role

AI toolspipeline managementoutbound prospectingROI modeling

Optimize my Resume

Apply Faster with Autofill

Free

Save your profile once. LumiJobs pre-fills the employer's application form so you stop re-typing the same answers on every site.

Apply With Autofill

Or skip LumiJobs's tools and submit directly on the employer's career site.

Apply on Employer Site

Enterprise Account Executive, Upper Mid-Market at Checkr · LumiJobs