Benefits Specialist

About Intellistack

At Intellistack, we're committed to revolutionizing the way organizations collect information, automate workflows, and create seamless digital experiences.

Founded with the belief that work should be simplified, Intellistack has grown into a leading provider of powerful, no-code productivity solutions that help teams do more with less. Across thousands of organizations worldwide, our tools and platform empower users to quickly build custom forms, automate document generation, capture eSignatures, and streamline data-driven processes—all without needing to write a single line of code.

With intuitive solutions that put power in the hands of everyday users, we make it easier to build, automate, and optimize processes at scale.

Who We Are
At Intellistack, we don’t do status quo. We move fast, think deep, and build what’s next—powered by people, supercharged by AI.

We’re a team of builders: curious, driven, and relentless about solving the real problem. Around here, feedback is fuel, clarity wins, and change is the default setting. If you’re hungry to grow and ready to leave a dent, you’ll fit right in.

Who You Are

As the Benefits Specialist, you’ll own end-to-end benefits operations across our U.S. and Canadian teams, with a primary focus on our self-insured U.S. health and welfare programs. You’ll manage everything from day-to-day administration and compliance filings to renewals, vendor relationships, and employee support.

This role is perfect for someone who loves details, thrives in complexity, and takes pride in helping employees navigate benefits with clarity and confidence. You’ll be the go-to expert for benefits operations, serving as the bridge between HR, Finance, and our external partners to ensure every part of our programs runs smoothly, accurately, and compliantly.

What You’ll Do

Program Management & Compliance

• 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

Data & Financial Analysis

• 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

Employee Experience

• 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
  

Operational Excellence

• 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 You Bring

• 4+ years of experience managing self-insured U.S. benefit plans (required)

• HRIS experience (Rippling strongly preferred)

• Strong understanding of medical, dental, stop-loss, and claims administration

• Familiarity with Canadian benefits programs and global coordination (preferred)

• 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

Why You’ll Love It Here

We’re human—supercharged. You’ll join a global team that values curiosity, speed, and impact.

• Flexible PTO and wellness benefits that support you and your family

• Professional development stipend and AI training access

• Hybrid work model with in-office collaboration Tuesday–Thursday

• Inclusive culture where your ideas move the business forward
  

Salary Range: $75,000–$100,000 (based on skills, experience, and location)

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.

We strongly encourage individuals from all backgrounds — especially women, people of color (including bilingual and bicultural individuals), LGBTQ+ persons, and people with disabilities — to apply. Even if you don’t meet every single requirement, you might be the right candidate for this or other roles.