Sr. People Operations and Systems Generalist

About the Role

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 critical moments such as getting a new job, a new place to live, a car ride, childcare, or even a date. Customers include Uber, Pennymac, Airbnb, Doordash, and Anthropic. We’re seeking a driven Senior People Operations and Systems Generalist to own the process side of our Workday ecosystem, translating business needs into well-designed processes and determining when gaps require simple ad-hoc tools versus technical builds from our Workday Product Analyst and internal systems team.

Beyond systems, you'll manage employee requests through our JIRA help desk, maintain data integrity across our people technology, and support compliance-related activities for the People Ops team. We're looking for someone who wants real ownership of a core people system with the room to build and is passionate about the details as Checkr continues to grow.

Responsibilities

• Serve as the functional Workday expert for the People Ops team, owning business process design from requirements through configuration, testing, and post-launch iteration.
• Own configuration, testing, and rollout for semi-annual Workday releases, proactively flagging opportunities to simplify or automate existing processes.
• Partner with the Workday Product Analyst and internal systems team on larger technical projects and integrations (e.g., Envoy to Workday), representing the People Ops perspective.
• Stand up simple, ad-hoc tools within the team's own toolkit (Sheets, trackers, JIRA workflows) to close process gaps, escalating true technical development to internal systems.
• Use tools like Lovable and Claude to rapidly prototype and build People Ops tools and automations, turning process ideas into working solutions on fast, business-critical timelines.
• Manage day-to-day Workday data and configuration, from position detail changes and EIB processing to troubleshooting, escalating architectural or security group changes to internal systems.
• Maintain up-to-date process documentation and deliver training materials for new system enhancements.
• Provide employee and manager support for complex or system-specific JIRA help desk tickets escalated from the team, representing company policies and practices.
• Prepare, review, and analyze data and reports, making recommendations in partnership with the Data Analyst (e.g., attrition and exit interview reporting).
• Own the immigration vendor relationship, support compliance, multi-state policy, and handbook administration.
• Serve as a backup layer for complex workplace compliance investigations escalated by HRBPs or the broader People Ops team.
• Support the Total Rewards team on compensation, benefits, equity, and leave administration, and partner with the Data Analyst on EEO-1 and Affirmative Action Plan reporting.
• Support the People function through ongoing process improvements and general team support.

Requirements

• Deep functional expertise in Workday HCM, with proven experience owning a process from idea through requirements, testing, and rollout, not just executing pre-defined configuration tickets. Additional Workday module experience is a strong plus.
• Comfort partnering with a technical systems team, translating business needs into requirements and testing plans rather than writing the build yourself.
• Familiarity with AI-assisted, no-code/low-code tools such as Lovable and Claude, using them to build lightweight People Ops solutions that drive high-impact outcomes quickly.
• 5+ years of experience in People Ops or systems-adjacent teams at fast-paced, scaling organizations.
• Expertise across broader people tools including JIRA Help Desk, Greenhouse, CultureAmp, and more.
• High degree of customer obsession, with a track record for delivering results, team collaboration, and business acumen.
• Problem-solving and critical-thinking skills, sound judgment, and a bias for action.
• Proven experience handling confidential information with discretion, honesty, and integrity.
• Proven time management and project management skills, with the ability to manage a high volume of requests and shifting priorities.
• Working knowledge of Google Suite required, especially Google Sheets (including v-lookups, pivot tables, and beyond).
• 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

We use geographic cost of labor as an input to develop ranges for our roles, and each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but will specify the target range for an exact location when you are selected for a recruiting discussion.

On-target Earnings OR Base Salary range (San Francisco, CA): $128,000 - $151,000 USD

Benefits

• 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

Schedule

At Checkr, we believe an in-office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.