Benefits Manager

Based in San Francisco; hybrid; in-office 4 days per week

About Abby Care

Making family care possible. At Abby Care, we are tackling one of the most important and unsolved challenges of our time: family caregiving.

Over 50 million Americans are family caregivers for loved ones without pay, tools, or support. Our mission is clear and ambitious: to train and employ family caregivers so they can get paid for the care they already provide at home.

Abby Care is building a tech-powered, family-first care platform to efficiently deliver care, improve health outcomes, and provide the best-in-class experience nationwide.

We are rapidly expanding our mission and looking for passionate team members to join. Abby Care has partnered with leading insurance plans, healthcare providers, and community organizations. We’re supported by top, mission-driven VCs to empower families throughout the country.

The Role

We are looking for a hands-on Benefits Manager to build and lead our benefits function during a critical phase of hypergrowth. This is a full-time hybrid position based in San Francisco, CA.

At Abby Care, our benefits program is more than just a package of perks: it is a key pillar of support for our people. For our corporate team, our benefits must remain competitive to attract world-class talent; for the qualifying caregivers who work full-time with us, these benefits provide critical stability and security for their own families.

Reporting to the Director of People Operations and Programs, you will own and drive our benefits programs for a diverse workforce. This includes salaried HQ and clinical employees as well as a rapidly growing population of hourly caregivers.

We need a leader who can balance full-stack execution with high-level strategy. You will dive deep to understand and manage our current benefits landscape, ensuring every enrollment and inquiry is handled with precision. Simultaneously, you will look forward to drive our strategic roadmap: identifying opportunities to consolidate systems and build scalable infrastructure, while unlocking economies of scale to design competitive, sustainable, and thoughtful programs that grow with us.

Key Responsibilities

• Scale Systems and Processes: You will assess our current landscape and lead the charge on streamlining, consolidation, and sustainable program design. You will architect a thoughtful benefits infrastructure that reduces manual work and prepares us well for hypergrowth and enterprise complexity.

• Program Design and Optimization: You will drive the strategy for a competitive and sustainable benefits portfolio. You will leverage economies of scale to manage costs effectively, ensuring our offerings are attractive to top talent while remaining financially thoughtful and accessible for our caregivers.

• Total Workforce Administration: Manage end-to-end benefits operations for our diverse workforce. You will own the daily execution and data integrity across our various platforms, ensuring seamless and accurate coverage for both HQ employees and caregivers.

• Employee Experience and Support: Serve as the primary trusted resource for benefits inquiries. You will deliver high-touch, empathetic service to our team, ensuring caregivers and corporate employees alike feel supported and informed about their coverage.

• Leave of Absence Management: Oversee the full lifecycle of leaves in partnership with our external vendors. You will ensure smooth coordination between Payroll and People Ops to deliver a compliant, accurate, and compassionate experience.

• Regulatory Compliance and Strategy: Own the benefits compliance landscape for our multi-state, multi-EIN footprint. You will ensure all programs adhere to federal, state, and local regulations (including ERISA, ACA, and San Francisco HCSO) while managing specific benefits-related complexities, including overseeing rigorous ACA lookback reporting and non-discrimination testing to ensure our tiered benefit structures remain compliant at scale.

• Audit and Financial Partnership: Serve as the lead for benefits audits and reporting. You will partner with Finance to ensure accurate filings (e.g., Form 5500s) and maintain impeccable data hygiene to support financial rigor.

• Cross-Functional Collaboration: Partner closely with key stakeholders, including Finance, Legal, and Operations, to ensure a cohesive and compliant approach to our benefits strategy. You will drive alignment across teams, for example - working with Finance on budget and renewals, Legal on risk, and Ops leadership to ensure our programs practically support our caregiver teams. You will surface risks early and influence decision-making to gain stakeholder buy-in for strategic changes.

• Change Management and benefits education: Own the end-to-end communication strategy for our entire benefits lifecycle. You will translate benefits concepts into clear, accessible language, driving benefits literacy and engagement across our diverse workforce. From new hire onboarding to ad-hoc updates, you will ensure our caregivers and corporate team alike understand the full value and utility of their coverage.

• Team Leadership: You will architect and lead our Benefits function, hiring and developing a high-performing team to support our growth. You will set the standard for operational excellence, mentoring your team to deliver phenomenal support to our employees.

The Requirements

• Experience: 7+ years of progressive benefits experience, with at least 2+ years in a management or lead role. You have thrived in a high-growth startup environment and/or a complex healthcare organization where processes had to be built or rebuilt.

• Complex Workforce Management: You have managed benefits for a mixed workforce that includes salaried exempt employees and a large volume of hourly/non-exempt workers. You understand the operational and compliance nuances of variable-hour employees (e.g., ACA lookback measurement periods).

• Regulatory and Compliance Mastery: You have deep, practical knowledge of federal, state, and local regulations (ERISA, HIPAA, COBRA, SF HCSO). You have successfully managed non-discrimination testing and annual audits (Form 5500s) for complex plan structures.

• HRIS and Benefits Technology: You are proficient in modern HRIS and Benefits platforms (e.g., Rippling, ADP, UKG, Workday, etc.). You are comfortable navigating backend configurations and carrier integrations.

• Operational Agility: You are comfortable working in the "gray." You can execute a manual process today (like managing a complex leave or fixing an enrollment error) while designing the automated solution for tomorrow. You are a problem solver who fixes operational debt rather than avoiding it.

• Business Acumen and Financial Modeling: You don't just run reports; you apply strong business judgment to data. You can manipulate data in Excel/Google Sheets to model costs, audit enrollments across multiple EINs, and track eligibility, always connecting the numbers back to the financial health of the business and the ROI of our programs.

• Employee Experience and Communication: You are a clear, compassionate communicator. You can explain complex insurance concepts to a caregiver on a help ticket just as effectively as you present strategy to the Executive Team. You treat internal customer service as a priority.

• Vendor Partnership and Negotiation: Experience holding brokers and carriers accountable. You have negotiated renewals and managed relationships with major vendors and carriers to drive performance and value.

• Modern tech stack fluency: You thrive in a cloud-native environment. You are highly proficient in Slack and Google Workspace (G Suite), using them for rapid communication and real-time collaboration. You are comfortable navigating multiple SaaS platforms simultaneously and prefer agile, digital workflows over static files and email chains.

Bonus points for:

• Implementation Experience: Experience migrating benefits platforms (e.g., moving from mid-market tool to an enterprise system like Workday).