Why This Job is Featured on The SaaS Jobs
This VP remit sits at a core SaaS inflection point: translating a product company’s growth into durable people systems. The scope spans total rewards strategy alongside the operational backbone of HR technology, positioning the function as a data and systems discipline rather than a purely policy-led one. In a SaaS environment where recurring revenue models depend on consistent execution, this kind of role shapes how the organization scales decision-making, governance, and employee experience through tooling and process design.
For a career in SaaS, the long-term value is the combination of board-level compensation and equity work with hands-on ownership of the people tech stack. That blend builds fluency in how late-stage SaaS companies manage incentives, retention, and organizational design, while also developing the operational muscle to instrument HR with analytics, automation, and self-service patterns. The experience is highly transferable across SaaS businesses that standardize on platforms like Workday and increasingly apply AI to internal operations.
This role best fits a senior operator who prefers building systems, simplifying complexity, and using data to drive change across stakeholders. It will suit someone comfortable moving between strategy and execution, and motivated by modernizing internal platforms as a lever for scale. It is also a strong match for leaders who want broad ownership across rewards, payroll-adjacent operations, and HR technology governance.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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 wellness stipend
