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Manage the lifecycle of employees on leave through software platforms and provide troubleshooting support for employees and managers. Partner with internal experts to answer questions regarding federal and state leave laws, insurance, and company policies.
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
#LI-Remote
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.
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