Health & Benefits - Onboarding Specialist - SaaS (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
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.
Preferred Qualifications
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
Compensation & Benefits
$66,000-$70,000 per year