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Health & Benefits - Onboarding Specialist - SaaS (Remote)

March 19, 2026

The Onboarding Specialist supports partner and employer onboarding through our SaaS operating model. This role will be facilitating welcome calls, coordinating bulk HSA/Notional migrations, and collaborating cross-functionally to ensure successful implementations and smooth client transitions as we scale. You will lead day-to-day client engagement and manage onboarding milestones while partnering with the Sr. Onboarding Specialist for execution of the onboarding work. Together, you'll translate business goals into solution designs and system configuration, align integrations and security requirements, and drive operational readiness. Success is measured by on-time go-lives, technical quality, time-to-value, and customer outcomes (CSAT/NPS). Duties & Responsibilities: • Support the implementation of CDH benefits (HSA, FSA, HRA, etc.) for SMB and Mid-Market clients via strategic partners. • Coordinate bulk HSA and Notional migrations and ensure a seamless employer transition. • Contribute to partner implementation projects and cross-functional execution. • Collaborate with Sr. Onboarding Specialist and Technical team to translate business goals into scalable, secure solution designs and reference architectures. • Assess integration needs (APIs, SSO, webhooks, EDI integrations, STFP), and data mapping, capture client success criteria and onboarding scope. • Coordinate Partner administration and configuration touchpoints, ensuring they follow best practices. • Partner on integrations and data migration activities (mapping, transformation, quality checks); maintain issue logs and dependencies. • Support test strategy and UAT readiness aligned to onboarding milestones and client success criteria. • Assist with defect triage and resolution during testing phases; communicate status and risks to stakeholders. • Execute client-facing components of cutover and go-live under the Sr. Onboarding Specialist's launch plan; facilitate runbook walk-throughs and contingency/backout planning. • Coordinate hyper-care, adoption enablement, and operational handoff to Customer Success/Support. • Build and maintain trusted-advisor relationships with partners and employers; ensure they realize value from our platform. • Mitigate risks and prevent churn by identifying issues early and leading mitigation efforts; act as voice of the customer to provide product feedback. • Support ongoing status calls and drive strategies that improve client health and satisfaction. • Adapt as responsibilities evolve with scale; contribute to continuous improvement of onboarding processes and overall client experience. • Produce and maintain onboarding documentation and artifacts (diagrams, runbooks, interface specs) to support operational readiness and handoff. Education & Experience: • Bachelor's Degree preferred or equivalent experience. • 2-4 years of client service, onboarding, or SaaS implementation experience (benefits administration experience a plus). • Strong relationship and communication skills with internal and external clients. • Proven ability to prioritize, multi-task, and complete tasks within specified timelines. • Ability to solve complex issues independently and in a collaborative team environment; timely and accurate decision-making. • Strong follow-through and follow-up skills. • Proficiency with Microsoft Office Suite, Google Suite, Jira/Confluence. • Detail-oriented, organized, and dependable. • Exposure to modern SaaS architectures and integration patterns (multi-tenant, APIs, SSO, webhooks, EDI integrations, STFP), and data mapping. • Familiarity with Consumer Directed Health Benefits and related regulations. Skills & Abilities: • Adaptability: Comfortable with ambiguity and the evolving nature of a scaling environment. • Curiosity: Naturally curious and thrives on learning new things. • CDH Interest/Experience: Interest or experience in Consumer Driven Healthcare or adjacent industries. • Relationship Management: Motivation to build and manage long-term client relationships. • Implementation Interest: Eagerness to contribute to implementation processes for enterprise partners. Other Requirements: • Business travel (up to 5% annually) • Video meetings, as needed • Ability to work overtime as needed to successfully manage the department • Prolonged periods of sitting at a desk, talking during meetings, and working on a computer Apply tot his job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...