Senior People Ops Generalist

540•Arlington, VA

3d•Hybrid

About The Position

540 is seeking a Senior People Ops Generalist to manage the operational foundation of its People function. The company, with approximately 100 employees across 25+ states, develops software for federal missions. The role requires maintaining efficient processes, a strong culture, and ensuring seamless operations in payroll, benefits, employee support, management guidance, and compliance across all operating locations. The Senior People Ops Generalist will report to the Chief People Officer (CPO) and will be a key part of the core People Ops team. This role involves close collaboration with other departments across the employee lifecycle, from onboarding to offboarding. The company is currently transitioning from a PEO to Rippling ASO, taking on more responsibility for benefits, payroll, compliance, and employment risk. This transition presents an opportunity for the new hire to significantly shape the People Ops function, especially with an upcoming benefits plan year renewal and the establishment of in-house payroll. The role is not a fully established function but one in motion, with the authority to improve it.

Requirements

5+ years of progressive People Operations/HR experience.
At least 2 years of hands-on multi-state payroll experience.
Strong understanding of how wage and hour, leave, disability, final pay, reimbursement, and other employment requirements vary by jurisdiction.
Thoughtful, creative approach to People Ops, designing policies, processes, and programs around the company's people and culture.
Hands-on benefits administration experience, including open enrollment and experience supporting 401(k), leave, and employee lifecycle programs.
Working knowledge of FLSA, FMLA, ADA, wage and hour requirements, and relevant state-level employment requirements.
Ability to research and apply requirements when entering a new jurisdiction.
Demonstrated manager coaching and employee relations experience, including guiding managers through performance concerns, documentation, difficult conversations, warnings, and/or performance improvement plans.
Proficiency with a modern HRIS/payroll platform such as Rippling, Paylocity, Gusto.
Strong operational discipline and attention to detail when working with payroll, benefits, employee data, and compliance deadlines.
Sound judgment under ambiguity and the ability to handle highly sensitive employee and company information with complete discretion.
Strong plain-language communication skills.
Comfort operating in a lean People function where you’ll work throughout the full employee lifecycle.
Comfort using AI and automation as part of your day-to-day work.

Nice To Haves

PHR/SPHR, SHRM-CP/SHRM-SCP, CPP, or FPC certification.
People Operations experience within a mid-sized government contractor, including familiarity with federal contractor reporting requirements such as VETS-4212.
Experience supporting an HRIS implementation, PEO transition, or payroll migration; Rippling experience is a plus.
Experience administering a Medical Expense Reimbursement Plan (MERP).
Experience supporting a high-growth, geographically distributed organization.
Demonstrated experience delivering successful employee engagement, recognition, and/or employee experience programs, such as earning or maintaining Great Place to Work certification.

Responsibilities

Own benefits administration across medical, dental, vision, life, disability, FSA/HSA, Medical Expense Reimbursement Plan (MERP), and voluntary benefits, including enrollments, qualifying life events, and terminations.
Manage carrier invoice reconciliation, eligibility, and claims escalations.
Own open enrollment, including HRIS configuration, employee communications, and post-enrollment audits.
Administer the 401(k) program, including contribution funding, eligibility, loans, ACA measurement tracking, 1094-C/1095-C filing, COBRA, and state continuation requirements.
Run end-to-end semi-monthly payroll for approximately 100 employees across 25+ states with support from Rippling ASO, including regular payroll, off-cycles, retroactive pay, bonuses, and final pay.
Direct and verify Rippling’s work on state and local payroll tax registrations, withholding accounts, and unemployment insurance accounts as new jurisdictions are added.
Understand and apply state-specific employment and government contracting requirements, including pay frequency, final pay deadlines, expense reimbursement, wage and hour requirements, and pay transparency.
Own onboarding as an employee experience, focusing on the first 90 days and cultural integration.
Partner with the CPO on employee engagement surveys, owning their administration, analysis, and translation into actionable changes.
Own the perks and benefits program, assessing employee usage, retiring underutilized benefits, and providing recommendations at renewal.
Own day-to-day employee experience programs including Great Place to Work certification and Fortune/Inc submissions.
Support the recognition program (Red Hot Awards).
Partner with the Ops Coordinator on company culture initiatives like 540 Week.
Administer FMLA, state paid family and medical leave, paid sick leave, parental leave, and other company leave programs.
Run and document the ADA interactive process and coordinate workers’ compensation claims, injury reporting, and return-to-work processes.
Coach managers through performance concerns, including expectations, documentation, and difficult conversations.
Run the operational side of the employee feedback cycle, including timelines and set-up.
Serve as a trusted first point of contact for employee questions, concerns, and conflicts, handling sensitive information with judgment and discretion.
Maintain the employee handbook and state-specific addenda, and monitor legislative and regulatory changes across all operating states.
Own compliance requirements including EEO-1, OSHA 300/300A, VETS-4212, state new-hire reporting, pay transparency, pay-data reporting, employment verifications, unemployment claims, and classification reviews.
Serve as an administrator and power user of Rippling, owning data integrity, workflows, permissions, audits, and People reporting.
Use AI and automation to eliminate repetitive People Ops work, improve accuracy, and create more time for work requiring human judgment.