HRIS, Benefits & Leave Lead

Accompany Health is on a mission to give patients with complex needs the dignified, high-quality care they deserve but rarely receive. A primary, behavioral, and social care provider, Accompany Health walks alongside patients for their entire care journey, offering at-home and virtual care, as well as 24/7 support. Partnering with innovative payors, Accompany Health is powered by remarkable care teams, elegant technology, and a commitment to evidence-based practice. 

We build long-term relationships with our patients so they know, without question, that our team is here for them day or night, year after year. We focus on the health outcomes most important to our patients to make it clear that they lead the way.

To achieve our mission, we collaborate with community-based organizations, local providers, and health plans. Led by our empathetic care teams, guided by proven care models, and powered by our own technology, we deliver a level of service that our communities rightfully deserve but rarely receive. 

While our headquarters is in Bethesda, MD, our teams are distributed across the country. If you’re eager to make a tangible difference in people’s lives, to help correct long-standing disparities in health care, join us.

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