Senior People Operations and Systems Generalist

• We are looking for 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 knowing when a gap calls for a simple ad hoc tool versus a technical build 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, helping us scale as Checkr continues to grow
• 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

Benefits

• Parental leave
• Stock optoins
• Work from home opportunities
• Comprehensive Health Plans | We cover 100% of insurance premiums and offer generous parental and family leave
• Competitive Compensation | We offer competitive salaries and meaningful equity
• A Variety of Food and Snacks | Our culinary team serves a rotating menu for lunch each day, along with unlimited snacks and drinks
• Wellness Programs | We invest in the holistic well-being of every team member through education reimbursements, onsite massages, and physical therapy
• Flexible Paid Time Off | We want you to take the time you need to relax and recharge
• Fitness and Public Transport Reimbursement | We’ll cover your commute and help you stay active with our onsite gym or fitness provider of choice- 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
• Proven experience handling confidential information with discretion, honesty, and integrity
• 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
• Working knowledge of Google Suite required, especially Google Sheets to include v-lookups, pivot tables, and beyond
• 5+ years of experience in People Ops or systems adjacent teams at fast paced, scaling organizations
• Problem solving and critical thinking skills, sound judgment, and a bias for action
• Proven time management and project management skills, with the ability to manage a high volume of requests and shifting priorities
• 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
• Expertise across our broader people tools including JIRA Help Desk, Greenhouse, CultureAmp, and more
• Comfort partnering with a technical systems team, translating business needs into requirements and testing plans rather than writing the build yourself
• High degree of customer obsession, with a track record for delivering results, team collaboration, and business acumen