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 Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company . The Chief of Staff Role Reporting to and as a strategic extension of the CEO, you will collaborate with Checkr’s executive team to drive strategic alignment, set priorities, and help increase the speed and ambition of the business.

You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, supporting M A, and supporting enterprise sales. What you bring Leadership and execution A bias towards action, equally effective at setting direction and independently executing initiatives from start to finish Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one Track record of planning and executing complex initiatives with world class project management Track record of using AI to deliver impact Earns trust quickly with customers, executives, board members, and investors 10+ years of experience working at an executive level or equivalent track record Startup founder experience strongly preferred Strategic thinking Strong business experience and acumen.

Responsibilities

Lead strategic initiatives Lead the CEO's highest-priority initiatives, end to end, from planning through execution Pressure-test strategy with customer, competitive, and market research Extend the CEO Serve as a proxy for the CEO in internal and external meetings Collaborate tightly with other executive direct reports with a one team mentality Lead functions or initiatives during transitions or while key roles are being hired Take the pulse of the company and surface what the CEO needs to hear Collaborate with and coach other Checkr leaders Drive operational excellence Optimize current processes and drive efficiency Improve communication and coordination across strategic initiatives Effectively communicate complex topics to junior and executive audiences alike Build presentations and financial models that frame critical decisions, including investor pitch decks and company narratives for external communications

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.

Compensation

philosophy, see our website .

, 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, we believe an 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.

What We Offer

A fast-paced and collaborative environment Learning and development allowance Competitive cash and equity

Perks

are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages.