Enterprise Account Executive, Upper Mid-Market

Rozgoo; United States; Remote; USD 120,000 - 260,000; Full time

Job summary

Checkr is seeking an Enterprise Account Executive to drive new logo growth within the Enterprise segment (>5K employees). This is a full-cycle, high-complexity sales role where you will build pipeline, manage multi-thread deals, and quantify prospect pain into ROI-driven outcomes.

You will negotiate contracts from $50K to $1M, collaborate with Product, SE, CS and Executives, and travel to meet prospects and customers at events or facilities.

Qualifications

• Proven track record closing new Enterprise accounts with multi-year quota.

Responsibilities

• Own new business sales across an assigned book (200–300 accounts) with a self-sourced outbound motion.
• Run full-cycle Enterprise deals across the buying committee and coordinate internal resources to close.
• Quantify pain and anchor ROI in financial terms during sales conversations.
• Negotiate and close annual contracts ranging $50K–$1M.
• Plan post-sale activation with ramp milestones and consumption targets.

Skills

Enterprise sales

Full-cycle selling

ROI modeling

Negotiation

Travel readiness

Job description

About Checkr

Checkr is building the data platform to power safe and fair decisions. Over 140,000 companies and millions of people rely on Checkr for AI verification in the moments that matter most: getting a new job, a new place to live, a car ride, childcare, even a date. Customers include Uber, Pennymac, Airbnb, Doordash, and Anthropic.
We're a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

As an Enterprise Account Executive, you'll own new logo growth within Checkr's Enterprise segment (>5K employees). This is a full-cycle, high-complexity sales role — you'll build pipeline, run sophisticated sales cycles, quantify prospect pain in financial terms, and stay accountable for the deal through post-sale activation. We're looking for someone who is AI-native, resourceful, and treats ramp and adoption as part of the sale, not someone else's problem.

What you'll do

• 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

What you bring

• Proven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to