Leave Success Specialist (HR/Healthcare) - Remote - Nov Start - $24/Hr

Job Description

ATTENTION MILITARY AFFILIATED JOB SEEKERS - Our organization works with partner companies to source qualified talent for their open roles. The following position is available to Veterans, Transitioning Military, National Guard and Reserve Members, Military Spouses, Wounded Warriors, and their Caregivers. If you have the required skill set, education requirements, and experience, please click the submit button and follow the next steps.

This is a remote role, but the following locations are excluded:

OCONUS - EU Countries

California

District of Columbia

Illinois

Montana

Rhode Island

Must have: 1-2 years of experience in a customer success or support role in a heavily regulated organization or complex subject matter – like human resources, healthcare, or law, plus all other noted qualifications.

As a member of the Leave Success Team you will have a few years of experience in a customer-facing role, preferably in the healthcare or human resources industry, and a passion for helping people when it matters most. You are highly organized and thrive in an environment where your ability to empathize, research, and serve others is celebrated.

Day in the Life

Managing the lifecycle of employees on leave through the customer's software and various support channels

Providing troubleshooting support for employees and their managers

Partnering with internal experts to serve as a resource for employees on leave - answering questions around U.S. state and federal leave laws, state paid family and medical programs, healthcare providers, insurance carriers, and company policies

Advocating for the customer internally by working across multiple departments

Ongoing development of your platform and industry knowledge around leave management and compliance

Collaborating with each account’s Customer Success Manager (CSM) to help prove value to our stakeholders

Communicating directly with regulatory agencies, healthcare and insurance providers, and other third parties if/when necessary

Auto req ID

485458BR

Minimum Education Required

High School/GED

Additional Qualifications/Responsibilities

Must Haves:

1-2 years of experience in a customer success or support role in a heavily regulated organization or complex subject matter – like human resources, healthcare, or law

Passion for helping people solve their problems and navigate abstract regulations

Ability to research policies and compliance literature – interpreting and translating knowledge to a non-policy savvy audience

Clear, articulate, and empathetic communication style – you deliver your message with respect, confidence, and compassion

Thrive in a fast paced environment, embrace technology and enjoy learning new tools and are able to easily change gears and switch between multiple platforms to get the job done

Naturally self-directed, organized, and resourceful with the ability to multitask, managing and switching priorities as needed

You thrive in a collaborative environment where diversity and inclusion is celebrated

Preferred Skills

Experience working in a remote environment

You have experience working with a startup and/or with a B2B SaaS business

You’re familiar with the leave compliance space

Competencies

Health & Family First

You've proven to be able to integrate all aspects of your life in a way that produces excellent work and ensures you care for what matters most in your life

You get things done at a pace consistent with the business needs

You consistently show up prepared, dependable and follow through on commitments

Autonomy + Team. Always

You are highly organized and can manage multiple priorities and deadlines at once

You are focused on scale and building - you understand that pace is equally as important as quality

Be Curious

When you don’t have all of the answers, you dig in and ask questions

You don’t let negative assumptions drive your actions and instead assume positive intent and find truth

You are intentional in discovering the paths of self-development we have to offer and seek out opportunities to engage in professional growth

Love Our Customers

You lead with empathy and compassion, meeting customers where they are and supporting them with intention and care

You take the time to deeply understand customers’ needs, goals, and challenges, not just the task at hand

You communicate openly and honestly, even when conversations are difficult

Fearlessly Flexible

You embrace change and navigate ambiguity with confidence and curiosity

You take initiative and make progress even when direction isn’t fully defined

Pay Rate: $24/hour

Start Date: Early November 2026

Schedule: 8am - 5pm | Monday - Friday in any US timezone

Training: 4-6 weeks | Monday-Friday 8am - 5pm MST

Equipment is provided!

Compliance & Eligibility

Background Check & Screenings: Successful candidates must complete and pass a background check and drug screen prior to their start date

Verification: In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification form upon hire.

Work Environment: Because this is a remote work role, you must have a private, dedicated workspace that enables you to work independently and without interruptions.

City*

United States

State*

N/A

Job_Category

Work From Home

Job Code

Work_From_Home WFH

Affiliate Sponsor

Instant Teams