Chief of Staff

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. You love business as a science Strong data analysis and problem-solving skills Exceptional, concise written and verbal communication 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