Chief of Staff

<div class="content-intro"><p><span style="font-weight: 400;"><strong>About Checkr<br></strong></span>Checkr is building the data platform to power safe and fair decisions. Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including Amazon, DoorDash, Netflix, Kimpton, and Anthropic.<br><br>We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on <a href="https://www.forbes.com/lists/cloud100/" target="_blank">Forbes Cloud 100 2025 List</a> and is a Y Combinator 2024 <a href="https://www.ycombinator.com/blog/yc-top-companies-2024">Breakthrough Company</a>.</p></div><p>Reporting to and as a strategic extension of the CEO, the Chief of Staff will be a force multiplier for Checkr’s leadership team. You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, and supporting M&amp;A. As the right hand to the CEO, you will collaborate with Checkr’s executive team to drive strategic alignment, set priorities, and boost productivity across the business.</p> <p><strong>What you bring</strong></p> <p><em>Strategic thinking</em></p> <ul> <li>Strategic pattern-matching across ambiguous, evolving problems, often in low-information environments. Zooms out to see the system at the meta level, zooms in as needed to execute</li> <li>Strong data analysis and problem-solving skills</li> <li>Exceptional written communication. Can turn ambiguity into a clear one-pager</li> </ul> <p><em>Leadership and execution</em></p> <ul> <li>Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one</li> <li>Track record of planning and executing strategic initiatives with operational excellence</li> <li>Track record of using AI to deliver impact</li> <li>Earns trust quickly with executives, board members, and external stakeholders</li> <li>10+ years of experience working at an executive level or equivalent track record</li> </ul> <p><em>Bonus</em></p> <ul> <li>Entrepreneurial and product leadership background</li> <li>Consulting experience</li> </ul> <p><strong>Responsibilities</strong></p> <p><em>Lead strategic initiatives</em></p> <ul> <li>Lead the CEO's highest-priority initiatives, end to end, from planning through execution</li> <li>Stand up new functions, products, or business lines from zero to one</li> <li>Pressure-test strategy with customer, competitive, and market research</li> </ul> <p><em>Extend the CEO</em></p> <ul> <li>Serve as a proxy for the CEO in internal and external meetings</li> <li>Collaborate tightly with other executive direct reports with a one team mentality</li> <li>Lead functions or initiatives during transitions or while key roles are being hired</li> <li>Take the pulse of the company and surface what the CEO needs to hear</li> <li>Collaborate with and coach other Checkr leaders</li> </ul> <p><em>Drive operational excellence</em></p> <ul> <li>Optimize current processes and drive efficiency</li> <li>Improve communication and coordination across strategic initiatives</li> <li>Effectively communicate complex topics to junior and executive audiences alike</li> <li>Build presentations and financial models that frame critical decisions, including investor pitch decks and company narratives for external communications.</li> </ul> <p><strong>What you’ll get</strong></p> <ul> <li>A fast-paced and collaborative environment</li> <li>Learning and development allowance</li> <li>Competitive cash and equity compensation, and opportunity for advancement</li> <li>100% medical, dental, and vision coverage</li> <li>Up to $25K reimbursement for fertility, adoption, and parental planning services</li> <li>Flexible PTO policy</li> <li>Monthly wellness stipend</li> </ul><div class="content-pay-transparency"><div class="pay-input"><div class="description"><p><strong>Pay Transparency Disclosure</strong></p> <p><em>We use geographic cost of labor as an in