VP, Total Rewards & People Operations

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 . About the team/role We're looking for a forward-thinking, data-driven, and innovative leader to own and evolve Checkr's Total Rewards programs and People Operations. Reporting to the Chief Legal Officer & Head of People, this role sits at the intersection of strategy, execution and leadership; designing compensation and total rewards programs that attract, incentivize and retain high-performing talent while building the systems, processes, and technology backbone that powers the entire People function. This isn't your typical HR role. We need a builder and change champion who sees HR technology, AI, and automation as powerful levers to empower employees to drive impact and deliver results. You'll challenge the status quo, anticipate needs before they arise, leverage data for proactive insights, and create a People Operations ecosystem that is as innovative and high-performing as the product we build for our customers. What you’ll do Serve as a strategic partner to the CLO/Head of People in setting an innovative and data-driven people strategy to power the future of Checkr. Own Checkr’s Total Rewards strategy end-to-end, designing compensation, benefits, equity, and variable pay programs that scale, reward impact, and attract and retain high-performing talent Lead equity strategy and governance, partnering with leadership and the Board to define equity compensation strategy for a late-stage private company Drive the People technology ecosystem and data architecture, optimizing Workday HCM and adjacent tools with automation and AI to deliver a seamless employee experience Champion and enable a self-service-first employee experience, creating frictionless processes, tools, and training that empower employees and managers while boosting adoption and satisfaction Lead a high-performing Total Rewards and People Operations team across payroll, people systems, benefits, reporting, and analytics, fostering a culture of ownership and growth Partner with senior leaders to scale rewards, processes, and People infrastructure and keep Checkr at the forefront of people strategy and innovation What you bring 5+ years of progressive experience spanning Total Rewards, People/HR Operations, and HR Technology, with 10+ years in senior leadership, ideally in high-growth or pre-IPO/public company environments Deep expertise in designing and executing a toward rewards strategy, including experience in innovating in compensation design Proven ability to build, scale, and optimize HR technology ecosystems, including connected platforms across ATS, benefits, compensation, and performance, driving efficiency and insight A tech-forward mindset with hands-on experience deploying AI, automation, and analytics to transform HR processes, systems, and employee experiences Exceptional communication and influence, able to translate complex ideas into simple, actionable insights and build trust across individual contributors, executives, and the Board Experience working with the Board and Compensation Committee on executive compensation and equity plan design for late-stage private companies is preferred but not required 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 locati