💼 Employment Type: Full-Time
📍 Location: Remote (U.S.)
💬 Job Overview
Intellistack — a fast-growing, no-code automation and workflow platform — is hiring a Benefits Specialist to own end-to-end administration for their U.S. and Canadian teams. This role centers heavily on self-insured U.S. medical and welfare plans, ensuring accuracy, compliance, and a great employee experience across all benefits programs.
You’ll manage everything from open enrollment, filings, claims analysis, and vendor partnerships to day-to-day employee support. The ideal candidate is detail-obsessed, loves navigating complexity, and excels at simplifying benefits information for employees. If you enjoy being the go-to expert and ensuring systems run flawlessly behind the scenes, this is a strong fit.
📋 Key Responsibilities
Program Management & Compliance
Administer U.S. and Canadian benefit programs, including medical, dental, vision, life, disability, and wellness plans.
Lead annual open enrollment planning, communications, and employee education.
Oversee required filings: ACA (1094-C/1095-C), MA 1099-HC, RxDC, Medicare Part D, PCORI, Form 5500, FSA nondiscrimination testing, and WRAP.
Support 401(k) plan administration, disclosures, and audits.
Manage state/local reporting (e.g., CA Pay Data, SF Healthcare Ordinance).
Partner with brokers, carriers, TPAs, and vendors to ensure compliance and accuracy.
Data & Financial Analysis
Conduct quarterly claims, cost, and utilization analyses.
Partner with Finance to forecast expenses, model plan scenarios, and understand trends.
Provide reporting and insights to inform benefit strategy.
Employee Experience
Serve as the primary contact for benefits questions, QLEs, 401(k) inquiries, coverage letters, HSA/FSA questions, and escalations.
Coordinate issue resolution with vendors to ensure excellent service.
Create clear, accessible benefits education and resources.
Operational Excellence
Reconcile invoices and resolve discrepancies across systems.
Maintain accurate benefits records in Rippling and other platforms.
Continuously improve processes for efficiency, accuracy, and compliance.
🧩 Requirements
4+ years managing self-insured U.S. benefit plans (required).
HRIS experience; Rippling strongly preferred.
Solid knowledge of medical, dental, stop-loss, and claims administration.
Familiarity with Canadian benefits and global coordination (preferred).
Deep understanding of ACA, ERISA, HIPAA, COBRA, and related regulations.
Experience working with brokers, carriers, and TPAs.
Strong analytical skills, comfortable with modeling and interpreting claims data.
Clear communicator with a service-oriented approach.
Ability to handle confidential information with discretion.
✨ Why You’ll Love This Job
Intellistack is a fast-moving, AI-powered, builder-centric company where you’re encouraged to innovate, solve hard problems, and lean into growth. They offer flexible PTO, wellness benefits, a professional development stipend, and an inclusive culture where every voice matters. With a hybrid structure (Tue–Thu office option), you’ll have flexibility plus meaningful collaboration.
🌟 Who This Job Is Perfect For
Benefits professionals who thrive on detailed work and accuracy.
Candidates comfortable owning complex, self-insured benefit programs.
HR/People Ops pros who enjoy becoming the subject-matter expert.
Individuals who value clarity, compliance, and helping employees navigate benefits.
Analytical, process-oriented thinkers who love optimizing systems.
🏢 About the Company
Intellistack helps thousands of organizations build automated workflows, forms, document generation tools, and eSignature processes — all without writing code. Their platform empowers everyday users to streamline operations and scale efficiently. Backed by a culture of curiosity, clarity, and fast execution, Intellistack is shaping the future of seamless digital experiences.
