Hris, Benefits & Leave Lead

About the role:

Our care teams show up for patients around the clock. This role makes sure we show up for them — that their data is right, their benefits work, and when life happens, their leave or accommodation is handled with clarity and care.

As the HRIS, Benefits & Leave Lead, you will own three connected areas of People Operations:

• HRIS: You are our Rippling expert — the person who knows the platform inside and out, leads every configuration change and integration, and builds the reporting our leaders rely on.
• Leave & Accommodations: You will bring leave of absence and ADA accommodation administration in-house from our current vendor, and become the trusted, employee-facing partner for every leave and accommodation request.
• Benefits: You will run day-to-day benefits administration and lead our partnership with our benefits broker to shape plans that fit a growing, distributed workforce.

You’ll work closely with People leadership, Business Leaders, Payroll, Finance, and IT.

Responsibilities will include: 

Leave of Absence & ADA Accommodations:

• Lead the transition of leave and accommodation administration from our external vendor to an in-house program, including process design, employee-facing materials, templates, tracking, and a clean handoff of open cases
• Serve as the primary, employee-facing point of contact for all leave requests — medical, parental, family care, military, and state-mandated leaves — guiding employees from first notice through return to work
• Manage the ADA interactive process end to end: intake, medical documentation, partnering with managers to identify effective accommodations, and documenting the dialogue and outcome. Escalate complex cases to People leadership and legal counsel
• Determine eligibility and track entitlements under FMLA, the ADA, and applicable state and local leave and paid family and medical leave programs across a multistate workforce
• Partner with Payroll and Finance to ensure pay during leave is accurate and confirmed — including PTO usage, salary continuation, disability and state benefit coordination, benefit premium deductions while on leave, and reinstatement at return to work
• Coordinate with disability carriers and state agencies on claim status and required filings
• Maintain medical and accommodation records confidentially and separately from personnel files
• Track leave and accommodation trends, and recommend policy and process improvements

Benefits Administration & Strategy:

• Own day-to-day benefits administration: new hire enrollment, qualifying life events, terminations, COBRA, and carrier data feeds
• Serve as the first point of contact for employee benefits questions — triage, resolve, and escalate to the broker or carriers when needed, with fast and empathetic follow-through
• Lead the working relationship with our benefits broker: bring utilization, cost, and employee feedback data to renewal discussions, evaluate plan design options, and present recommendations to People leadership and Finance
• Run annual open enrollment end to end: plan setup in Rippling, employee communications and education, and post-enrollment audit
• Reconcile monthly benefits invoices against enrollment data and resolve discrepancies with carriers and the broker
• Ensure compliance with ACA (including 1094-C/1095-C reporting), COBRA, ERISA, HIPAA privacy, Section 125, and required employee notices, in partnership with our broker and counsel

HRIS & People Data (Rippling):

• Serve as Accompany’s Rippling owner and subject-matter expert across all modules in use: configuration, custom fields, policies, workflows, approval chains, and user permissions
• Own intake, prioritization, and delivery of all HRIS change requests, assessing downstream impact on payroll, benefits, and reporting before anything goes live.
• Lead integrations between Rippling and connected tools (e.g., Greenhouse, benefits carriers, payroll, finance, and IT/identity systems): scope requirements, coordinate with vendors, test, and monitor data feeds over time
• Design and build sophisticated reports and dashboards — headcount, turnover, compensation, leave, benefits cost and utilization, and compliance reporting (e.g., EEO-1, ACA) — and translate the data into clear insights for People leadership, Finance, and executives
• Protect data integrity through regular audits, documented controls, and role-based access based on least privilege, with particular care for sensitive and medical information
• Evaluate new Rippling functionality and automation opportunities; recommend and lead rollouts and upgrades
• Document configurations, integrations, and processes so our systems scale and knowledge never lives in one person’s head
• Train and support employees and People team members on self-service functionality

What makes you a fit for the team: 

• You take ownership of accuracy. Data, pay, and compliance details matter to you because you know they matter to people
• You’re a builder. You’ve stood up processes from scratch and you like making them better
• You meet people well in hard moments. Employees come to you during illness, new parenthood, and family crises; you respond with warmth, clarity, and discretion
• You translate complexity. You can explain a system change to IT, a leave entitlement to an employee, and a cost trend to Finance
• You’re comfortable in a fast-paced, evolving environment and can prioritize across competing demands
• You’re motivated by supporting a mission-driven organization scaling to serve more patients and communities

What success looks like: 

• First 90 days: You own the Rippling change queue, have completed an audit of core data and permissions, mapped every integration, and inventoried open leave cases with our current vendor
• First 6 months: Leave and ADA administration is running in-house with documented processes, templates, and a working pay-confirmation rhythm with Finance and Payroll
• First 12 months: You have led a full benefits renewal and open enrollment with data-backed recommendations, and a reporting suite is live for People leadership and Finance

Desired skills and experience

• Required
• Bachelor’s degree in Human Resources, Business Administration, Information Systems, or a related field, or equivalent experience
• 5+ years of experience across HRIS, benefits, and leave administration, with hands-on depth in at least two of the three
• 3+ years as a primary administrator of a modern HRIS, including configuration, workflows, permissions, and building complex reports
• Direct experience administering FMLA, managing the ADA interactive process, and handling state leave programs, ideally across multiple states
• Experience administering benefits and working directly with brokers and carriers, including open enrollment and invoice reconciliation
• Advanced analytical and data skills in Excel/Google Sheets (e.g., pivot tables, lookups, reconciliations)
• Working knowledge of ACA, COBRA, ERISA, and HIPAA requirements
• Excellent judgment, discretion, and communication with both technical and non-technical audiences
• Preferred
• Expert-level Rippling administration, including custom workflows, custom fields, and report building
• Experience with Rippling, Greenhouse, and Google Workspace
• Experience building or managing system integrations (payroll, benefits, ATS) and working knowledge of APIs, data feeds, or automation tools
• Experience bringing leave administration in-house or transitioning between leave vendors
• Relevant certifications such as CLMS (Certified Leave Management Specialist), CEBS, SHRM-CP/SCP, or PHR/SPHR
• Experience supporting a clinical or 24/7 workforce, or a background in healthcare, health tech, or a high-growth startup