Intellistack is looking for a Benefits Specialist to own end-to-end benefits operations across our U.S. and Canadian teams. Your primary focus will be on managing our self-insured U.S. health and welfare programs, serving as the go-to expert who bridges HR, Finance, and external partners.

What You'll Do

Administer and maintain all U.S. and Canadian benefits programs, including self-insured medical, dental, vision, life, disability, and wellness.
Lead annual open enrollment, including planning, communications, and employee education.
Oversee required filings and compliance, including ACA (1094-C/1095-C), MA 1099-HC, RxDC, Medicare Part D, PCORI, Form 5500, WRAP, and FSA non-discrimination testing.
Support 401(k) plan administration, audits, and disclosures.
Manage state and local reporting (e.g., CA Pay Data, San Francisco Healthcare Ordinance).
Partner with brokers, TPAs, and carriers to ensure compliance, accuracy, and strong service delivery.
Run quarterly claims, utilization, and cost analyses to identify trends and opportunities.
Partner with Finance to forecast plan expenses, track funding, and model future scenarios.
Provide reporting and insights to support plan design and decision-making.
Serve as the primary contact for employee benefits questions and requests, including QLEs, 401(k) inquiries, proof-of-coverage letters, and HSA/FSA issues.
Manage escalations with vendors to ensure timely resolution and a positive employee experience.
Simplify benefits communication and education through clear, accessible resources.
Reconcile invoices and resolve discrepancies across multiple vendors and systems.
Maintain accurate records in Rippling and related systems.
Continuously assess and improve processes for efficiency, accuracy, and compliance.

What We're Looking For

4+ years of experience managing self-insured U.S. benefit plans.
HRIS experience.
Strong understanding of medical, dental, stop-loss, and claims administration.
Deep knowledge of ACA, ERISA, HIPAA, COBRA, and related compliance requirements.
Experience working with brokers, carriers, and third-party administrators.
Analytical mindset; comfortable with cost modeling and claims data.
Clear, confident communicator with a customer-first approach.
Proven ability to manage confidential information with discretion and accuracy.

Nice to Have

HRIS experience with Rippling.
Familiarity with Canadian benefits programs and global coordination.

Technical Stack

Rippling

Team & Environment

You'll bridge between HR, Finance, and external partners.

Benefits & Compensation

Compensation: $75,000–$100,000
Flexible PTO and wellness benefits that support you and your family.
Professional development stipend and AI training access.
Inclusive culture where your ideas move the business forward.

Work Mode

This is a hybrid position with in-office collaboration Tuesday–Thursday, open to candidates in the U.S. and Canada.

Intellistack is an equal opportunity employer, passionately committed to equitable hiring and boldly dedicated to diversity in our work and teams. We do not discriminate in employment opportunities or practices based on actual or perceived race, color, religion, national origin, sex (including pregnancy, childbirth, or related conditions), age, marital status, sexual orientation, gender identity or expression, veteran status, uniformed service member status, disability, or any other characteristic protected by law.