Health & Benefits – Onboarding Specialist – SaaS

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