VP, Total Rewards & People Operations

About Checkr Checkr is building the data platform to power safe and fair decisions. Established in 2014, 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 DoorDash, Coinbase, Lyft, Instacart, and Airtable. 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 and retain world-class 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 reimagine how employees experience Checkr. 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 modern and innovative as the product we build for our customers. What you’ll do Own Checkr’s Total Rewards strategy end-to-end, designing compensation, benefits, equity, and variable pay programs that scale, reward impact, and attract top 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 10+ years of progressive experience spanning Total Rewards, People/HR Operations, and HR Technology, with 5+ 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 Experience working with the Board and Compensation Committee on executive compensation and equity plan design for late-stage private companies 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 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 What you’ll get 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 we ... (truncated, view full listing at source)