Enterprise Account Executive, Upper Mid-Market

Checkr, Inc.; Chicago (IL); On-site; USD 252,697 - 297,290; Full time

Benefits offered by this job

Learning allowance

Equity compensation

Medical, dental, and vision coverage

Fertility & parental planning support

Flexible PTO

Wellness stipend

Career growth opportunities

Job summary

Checkr, Inc. is seeking an Enterprise Account Executive in the Chicago area to own new logo growth within the Enterprise segment (>5K employees). This full-cycle role demands building pipeline, managing complex deals, and quantifying ROI for executives.

You will lead cross-functional resources, drive AI-enabled prospecting, and travel to client sites as needed. Ideal candidates bring a proven enterprise closing track record, a self-sourced outbound motion, and the ability to articulate business

Qualifications

• Proven track record closing enterprise accounts with multi-year quota attainment.
• Self-sourced outbound motion and ability to generate pipeline.
• Experience selling to EVPs/CXOs and end-users in the same cycle.
• Ability to quantify business value and build ROI cases.
• Experience owning post-sale handoff and ramp planning.

Responsibilities

• Own new business sales across an assigned book (200–300 accounts).
• Run full-cycle Enterprise deals with multi-threaded stakeholders.
• Quantify prospect pain and anchor ROI in the deal.
• Negotiate and close annual contracts ($50K–$1M).
• Own post-sale ramp planning and handoff to CS.
• Leverage AI tools for research, pipeline, and prospecting.
• Develop internal champions and secure internal approvals.
• Travel to meet prospects and customers.

Skills

Enterprise sales

Outbound prospecting

Executive selling

ROI storytelling

Post-sale ramp planning

AI tools usage

HR buyers

Strong communication

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, Amazon, and Anthropic.

We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on the 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 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
• 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 Transparency Disclosure

We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.

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

• A fast‑paced and collaborative environment
• 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

Equal Employment Opportunities at Checkr

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

If you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.

• Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., [e-mail] or [e-mail]).